Author(s): H.-J. Timpe, K.-P. Kronfeld and R. Mahlow
Title: 3,6-Bis(dimethylamino)-thioxanthon - ein potentieller Photoinitiator
Z. Chem. Vol. 30, No. 2, p. 55-56 (1990); ISSN: 0044-2402; CODEN: ZECEAL

keywords: thiopyronine; thioxanthone; 3,6-bis(dimethylamino)-thioxanthone (BTX); 3,6-bis(dimethylamino)-thioxanth-9-one; 3,6-bis(dimethylamino)-thioxanthylium-chloride
longest wavelength absorption maximum of Michler's Ketone: 354 nm (Acetonitril) (e 37700 mol-1cm-1)
longest wavelength absorption maximum of Thioxanthone: 381 nm (Acetonitril) (e 6320 mol-1cm-1)
longest wavelength absorption maximum of BTX: 375 nm (Acetonitril) (e 54100 mol-1cm-1)

Author(s): J. Biehringer
Title: Über die Farbstoffe der Pyroningruppe
J. Prakt. Chem. Vol. 162 [54, Ser. 2], p. 217-258 (1896); ISSN: 0021-8383; CODEN: JPCEAO

keywords: Nitration of 4,4'-Bis(dimethylamino)-diphenylmethane; reduction of 2,3'-Dinitro-4,4'-bis(dimethylamino)-diphenylmethane with stannous in hydrochloric acid forming 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane; cyclisation of 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane forming 3,6-bis(dimethylamino)-acridine; oxidation of 3,6-Bis(dimethylamino)-acridine forming acridine orange; 3,6-Bis(dimethylamino)-acridinyl chloride

Author(s): J. Biehringer and W. Topaloff
Title: Über Thiopyronin
J. Prakt. Chem. Vol. 173 [65, Ser. 2], p. 499-511 (1902); ISSN: 0021-8383; CODEN: JPCEAO

keywords: thiopyronine; thioxanthone; 3,6-bis(dimethylamino)-thioxanthone (BTX); 3,6-bis(dimethylamino)-thioxanthylium-chloride; sulfuration of 4,4'-bis(dimethylamino)-diphenylmethane with sulfur introduced in fuming sulfuric acid; oxidation of 3,6-bis(dimethylamino)-thioxanthone forming 4,4'-bis(dimethylamino)-benzophenonsulfone
vergleiche Deutsches Reichspatent DE 65739; ebenso zur Sulfurierung/ Sulfonierung von 4,4'-Bis(dimethylamino)-diphenylmethan: DRP DE 65017, DRP DE 54621 and DRP DE 88085, sowie Jones, D.C.R.; Mason, F.A.: J. Chem. Soc. 1934, 1190-1192.

CAS No. BTX: [7031-01-8]

Author(s): F. Ullmann and A. Maric
Title: Über Diaminoacridiniumverbindungen. 4. Mitteilung über Acridine
Ber. dtsch. Chem. Ges. Vol. 34, p. 4307-4316 (1901); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Mono-nitration of 4,4'-Bis(dimethylamino)-diphenylmethane; nitration of 4,4'-Bis(dimethylamino)-diphenylmethane; reduction of 2-Nitro-4,4'-bis(dimethylamino)-diphenylmethane with stannous chloride in hydrochloric acid forming 2-Amino-4,4'-bis(dimethylamino)-diphenylmethane; reduction of 2,2'-Dinitro-4,4'-bis(dimethylamino)-diphenylmethane with stannous in hydrochloric acid forming 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane; cyclisation of 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane forming 3,6-Bis(dimethylamino)-acridine; acridine orange; 3,6-Bis(dimethylamino)-acridinium-chloride; alkylation of 3,6-Bis(dimethylamino)-acridine forming N-Methyl-3,6-bis(dimethylamino)-acridinium-methosulfate with dimethyl sulfate; methylation with dimethyl sulfate; 3,6-Bis(dimethylamino)-10-methylacridinium-methosulfate; 3,6-Bis(dimethylamino)-N-methylacridinium-iodide

Author(s): J. Pinnow
Title: Über Tetramethyldiamidodiphenylmethan
Ber. dtsch. Chem. Ges. Vol. 27, p. 3161-3167 (1894); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Einwirkung von salpetriger Säure auf 4,4'-Bis(dimethylamino)-diphenylmethan; Nitrierung von 4,4'-Bis(dimethylamino)-diphenylmethan; Reduktion von 2,2'-Dinitro-4,4'-bis(dimethylamino)-diphenylmethan mit Zinn in Salzsäure zu 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethan; 4,4'-Bis(dimethylamino)-diphenylmethan-2,2'-diamin; Herstellung von 4,4'-Bis(dimethylamino)-diphenylmethan durch Kondensation von Dimethylanilin mit Formaldehyd in Eisessig; Einwirkung von Formaldehyd auf 4,4'-Bis(dimethylamino)-diphenylmethan führt zu nicht identifizierten Produkten

Author(s): A. Kliegl
Title: Über die Nitroderivate des Tetramethyldiamidobenzophenons
Ber. dtsch. Chem. Ges. Vol. 39, p. 1266-1275 (1906); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Nitrierung von 4,4'-Bis(dimethylamino)-diphenylketon; 4,4'-Bis(dimethylamino)-benzophenon; Reduktion von 3,3'-Dinitro-4,4'-bis(dimethylamino)-diphenylketon mit Zinnchlorid in Salzsäure zu 3,3'-Diamino-4,4'-bis(dimethylamino)-diphenylketon; 3,3'-Diamino-4,4'-bis(dimethylamino)-benzophenon; Mono-Nitrierung von 4,4'-Bis(dimethylamino)-diphenylmethan; Acetylierung von 2-Amino-4,4'-bis(dimethylamino)-diphenylmethan zu 2-Acetamido-4,4'-bis(dimethylamino)-diphenylmethan; Oxidation zu 2-Acetamido-4,4'-bis(dimethylamino)-diphenylketon; 2-Acetamido-4,4'-bis(dimethylamino)-benzophenon

Author(s): P. Jakobsen, A.P. Andersen, H. Lyon and S. Treppendahl
Title: Preparation and characterization of Pyronin Y
Microscopia Acta Vol. 87, No. 1, p. 41-47 (1983); ISSN: 0044-376X; CODEN: MSACCU

keywords: condensation of 3-Dimethylaminophenol and formaldehyde forming 2,2'-Dihydroxy-4,4'-bis(dimethylamino)-diphenylmethane; cyclisation of 2,2'-Dihydroxy-4,4'-bis(dimethylamino)-diphenylmethane at 100 °C with sulfuric acid froming 3,6-Bis(dimethylamino)-xanthene; oxidation with salpetriger Säure zu 3,6-Bis(dimethylamino)-xanthylium-chloride; Pyronine G; Pyronine Y

Author(s): M.J.S. Dewar
Title: Colour and Constitution. Part I. Basic Dyes
J. Chem. Soc., p. 2329-2334 (1950); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Michler's Hydrolblau; Acrdinorange; Pyronin Y; Pyronin G; Malachitgrün; Methylenblau; Methylengrün
longest wavelength absorption maximum of Michler's Hydrolblue: 610 nm
longest wavelength absorption maximum of Acridine orange: 491 nm
longest wavelength absorption maximum of Pyronine G: 547,5 nm

___________________
Part II and Part III ca be found at:
Dewar, M.J.S.: 676. Colour and Constitution. Part II. Aromatic hydrocarbons. J. Chem. Soc. 1952, 3532-3544.
Dewar, M.J.S.: 677. Colour and Constitution. Part III. Polyphenyls, polyenes and Phenylpolymers; and the significance of cross conjugation. J. Chem. Soc. 1952, 3544-3550.

Author(s): V.K. Grif, V.M. Nikitchenko and V.F. Lavrushin
Title: Synthesis and spectroscopic investigation of Polymethine carbonium ions
J. Org. Chem. USSR Vol. 14, No. 6, p. 1197-1202 (1978); ISSN: 0022-3271; CODEN: JOCYA9
Zh. Org. Khim. Vol. 14, No. 6, p. 1293-1298 (1978); ISSN: 0514-7492; CODEN: ZORKAE

longest wavelength absorption maximum of Michler's Hydrolblue: 614 nm (e 152000 mol-1cm-1)

Title: Verfahren zur Darstellung eines Orange-Farbstoffes der Akridinreihe
(L. Leonhardt & Co., Mühlheim, Hessen, Deutschland) Dtsch. Reichspatent DE 59179, (21.09.1891); Patent Class.: C09B15/00

keywords: 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane, cyclisation of 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane forming 3,6-Bis(dimethylamino)-acridine, oxidation reaction forming Acridine orange, 3,6-Bis(dimethylamino)-acridinium-chloride

Title: Verfahren zur Darstellung eines rothen basischen Farbstoffes der Diphenylmethanreihe aus Tetramethyldiaminodiphenylmethan
(A. Gerber & Co., Basel, Schweiz) Dtsch. Reichspatent DE 60505, (19.12.1891); Patent Class.: C09B57/00

keywords: 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane, Cyclisierung von 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane zu 3,6-Bis(dimethylamino)-acridine, Oxidation zu Acridine orange, 3,6-Bis(dimethylamino)-acridinium-chloride, Nitrierung von 4,4'-Bis(dimethylamino)-diphenylmethane, Reduktion von 2,2'-Dinitro-4,4'-bis(dimethylamino)-diphenylmethane mit Zinkstaub 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane, Diazotierung von 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane zu einem Farbstoff unbekannter Struktur, Einwirkung von salpetriger Säure auf 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethane

Title: Verfahren zur Darstellung blaurother schwefelhaltiger Farbstoffe aus Tetraalkyldiamidodiphenylmethanen
(Joh. Rud. Geigy & Co., Basel, Schweiz) Dtsch. Reichspatent DE 65739, (08.11.1892); Patent Class.: C09B11/28

keywords: thiopyronine, 3,6-Bis(dimethylamino)-thioxanthylidene-chloride, Sulfurierung von 4,4'-Bis(dimethylamino)-diphenylmethan mit Schwefel in rauchender Salpetersäure zu 3,6-Bis(dimethylamino)-thioxanen, 3,6-Bis(dimethylamino)-thioxanthon, 3,6-Bis(dimethylamino)-thioxanth-9-one
vergleiche Biehringer, J.; Topaloff: J. Prakt. Chem. 173 [65, Ser. 2], 1902, 499-511.
zur Sulfurierung / Sulfonierung vergleiche DRP DE 65017, DRP DE 88085 and DRP DE 54621, sowie Jones, D.C.R.; Mason, F.A.: J. Chem. Soc. 1934, 1190-1192.

Title: Verfahren zur Darstellung von Säurederivaten von m-Amidoalkyldiamidobenzylhydrolen
(Bayer & Co., Elbernfeld) Dtsch. Reichspatent DE 79250, (12.01.1895)

keywords: Mono-Nitrierung von 4,4'-Bis(dimethylamino)-diphenylmethan, Nitrierung von 4,4'-Bis(dimethylamino)-diphenylmethan, Reduktion von 2-Nitro-4,4'-bis(dimethylamino)-diphenylmethan mit Zinkstaub in Salzsäure zu 2-Amino-4,4'-bis(dimethylamino)-diphenylmethan, Reduktion von 2,2'-Dinitro-4,4'-bis(dimethylamino)-diphenylmethan mit Zinkstaub in Salzsäure zu 2,2'-Diamino-4,4'-bis(dimethylamino)-diphenylmethan Acetylierung, Oxidation von 2-Acetamido-4,4'-bis(dimethylamino)-diphenylmethan zu Analogen von Michlers Hydrolblau

Author(s): A.K Arens, B.E Arens and G.J. Vanag
Title: A new method for the production of 2-arylidenindandiones-1,3
Dokl. Chem. (Engl. Transl.) Vol. 135, No. 2, p. 1263-1265 (1960); ISSN: 0012-5008; CODEN: DKCHAY
Dokl. Akad. Nauk. SSR, Ser. Khim. Vol. 135, No. 2, p. 320-322 (1960); ISSN: 0002-3264; CODEN: DASKAJ

Title: Verfahren zur Darstellung einer komplexen Aminoargentomercaptobenzolcarbonsäure
(E. Schering AG, Berlin) Dtsch. Reichspatent DE 377914, (29.07.1923); Patent Class.: C07C323/58

keywords: 4-Amino-2-mercaptobenzoic acid, 4-Aminothiosalicylsäure, Diazotierung von 4-Nitro-2-aminobenzoesäure, 4-Nitroanthranilsäure, Reduktion von 4-Nitro-2-thiocyanobenzoesäure zu 4-Aminothiosalicylsäure

Title: Verfahren zur Herstellung blauer Triphenylmethanfarbstoffe aus der Disulfosäure des Tetramethyldiaminodiphenylmethans
(Joh. Rud. Geigy & Co., Basel, Schweiz) Dtsch. Reichspatent DE 65017, (07.10.1892); Patent Class.: C09B11/16

keywords: Sulfurierung /Sulfonierung von 4,4'-Bis(dimethylamino)diphenylmethan zu 4,4'-Bis(dimethylamino)diphenylmethan-2,2'-disulfonsäure, 4,4'-Bis(dimethylamino)diphenylmethan-2-sulfonsäure, 3,6-Bis(dimethylamino)-thioxanthen-10,10-dioxid
Vergleiche DRP DE 54621, DRP DE 65739 and DRP DE 88085, sowie Jones, D.C.R.; Mason, F.A.: J. Chem. Soc. 1934, 1190-1192.

Title: Verfahren zu Darstellung von Tetramethyldiamidodiphenylmethansulfon
(Farbwerke vorm. Meister Lucius & Brüning in Höchst a. Main) Dtsch. Reichspatent DE 54621, (22.11.1890); Patent Class.: C09B11/16

keywords: Sulfurierung /Sulfonierung von 4,4'-Bis(dimethylamino)diphenylmethan zu 3,6-Bis(dimethylamino)-thioxanth-9-on-10,10-dioxid
Vergleiche DRP DE 65017 and DRP DE 88085, sowie Jones, D.C.R.; Mason, F.A.: J. Chem. Soc. 1934, 1190-1192.

Title: Verfahren zu Darstellung von Disulfonsäuren violetter Farbstoffe aus Diäthyldibenzyldiamidodiphenylmethansulfonsäure
(Joh. Rud. Geigy & Co., Basel, Schweiz) Dtsch. Reichspatent DE 59811, (31.10.1891); Patent Class.: C09B11/16


Vergleiche DRP DE 65017, DRP DE 54621und DRP DE 88085, sowie Jones, D.C.R.; Mason, F.A.: J. Chem. Soc. 1934, 1190-1192.

Title: Verfahren zur Darstellung von gelben bis braunen Farbstoffen der Akridinreihe
(Farbenfabrik vorm. Friedrich Bayer & Co., Ebernfeld) Dtsch. Reichspatent DE 114262, (05.10.1900)

Title: Verfahren zur Darstellung von gelben bis braunen Farbstoffen der Akridinreihe
(Farbenfabrik vorm. Friedrich Bayer & Co., Ebernfeld) Dtsch. Reichspatent DE 116353, (24.11.1900)


Dieses Patent ist ein Zusatzpatent zu DE114261.

Inventor(s): C.H. Chen and J.L. Fox
Title: Novel thiorhodamines and a novel method of preparation
(Eastman Kodak Co. USA) Eur. Pat. Appl. EP 0330444, (30.08.1989); Patent Class.: C07D335/12 ; C07D413/10
Klassifikationssymbol (EC) : C07D335/12, C07D413/10
CODEN: EPXXDW
keywords: Oxidation von 3,6-Bis(dimethylamino)-thioxanthen zu 3,6-Bis(dimethylamino)-thioxanth-9-on mit Kaliumpermanganat, BTX, 3,6-Bis(dimethylamino)-thioxanthon
corresponding patents: AU3008289, DK79389, FI890846, JP1254771, NO890761

Abstract:
There are disclosed novel thiorhodamines having the following structural formula: wherein R and R1 are individually H or alkyl of 1 to 5 carbon atoms, and Z is an anion. Also disclosed is the only known, and novel, method for making them, namely a) conducting an addition reaction between a thioxanthone and a compound having the formula: wherein R2 is alkyl of 1 to 5 carbon atoms; b) dehydrating the resulting compound of step a) in a strong acid to form a 9-[2-oxazolinylphenyl]thioxanthylium salt; c) hydrolyzing the oxazoline ring with acid to the 9-(2-carboxyphenyl)thioxanthylium salt; and d) optionally esterifying the resultant compound of step c) in an alkanol and strong acid, wherein the alkanol contains from 1 to 5 carbon atoms.

Inventor(s): C.T.-L. Chang
Title: Photopolymerizable compositions comprising initiator combinations comprising thioxanthones
(Du Pont, USA) US Pat. Appl. US 3926643, (16.12.1975); Patent Class.: G03C1/68 ; G03C1/70
Klassifikationssymbol (EC) : G03F7/031
CODEN: USXXDP
keywords: 3,6-Bis(dimethylamino)-thioxanth-9-one, BTX, 3,6-Bis(dimethylamino)-thioxanthone

Inventor(s): L. Benda and O. Sievers
Title: Compounds of the acridinium series and a process of preparing them
(Winthorp Chem. Co. Inc.) US Pat. Appl. US 2039577, (05.05.1936); Patent Class.: C07F9/70B, C07D219/06, C07D219/08
CODEN: USXXDP

corresponding patents: DE606498, FR755631, GB419632, GB41960

Title: Process for the manufacture of double compounds of the acridine series
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 348047, (27.04.1931); Patent Class.: C07D219/08
CODEN: BAXXDU

Abstract:
Double salts of 3,6-diamino-10-alkylacridinium bases with 3,6-diaminoacridine are obtained by alkylating to the extent of 50 % 3,6-diamino-acridine, substituted in the amino group by a substituent capable of being split off, and then eliminating the said substituent. The desired semi-alkylation is effected in a solvent using an amount of alkylating agent which is dependent upon the temperature conditions. With a temperature of 140 °C an equimolecular proportion is employed; above it the proportion must be diminished, whilst below it the proportion must be greater than equimolecular. Examples are given of the preparation of 3,6-diamino-10-methyl-acridinium chloride, 3,6-diaminoacridine hydrochloride and the corresponding sulphate, and 3,6-diamino-10-ethylacridiniumchloride, 3,6-diaminoacridine hydrochloride. 3,6-Diacetyl-diaminoacridine forms the starting material in each case, nitrobenzene and dichlorobenzene are employed as solvents, methyl sulphate and p-toluene-sulphonic methyl and ethyl esters comprise the alkylating agent, and after a heat treatment with a quantity of the alkylating agent which is determined by the temperature employed, the acetyl group is saponified with hydrochloric and sulphuric acid respectively.

Title: Manufacture of acridinium compounds
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 473843, (20.10.1937)
CODEN: BAXXDU

Abstract:
Acridinium compounds are made by heating a condensation product of a ketone and a 3,6-diaminoacridinium compound obtainable according to Specification 434,497 with an acid, acid salt, acid amide or a salt of a volatile base or by boiling it with water and treating the resulting acridinium hydroxide with a salt or an acid to form an acridinium salt or with an alcohol, phenol, alcoholate or phenolate to form an acridinium ether. Dilute acids split off the ketones gradually when allowed to stand at room temperature, and quickly when boiled, giving acridinium compounds of the acids employed, which may be acid if dibasic or polybasic acids are used. Volatile bases specified are ammonia, aniline, methylamine, dimethylaniline, and amides specified are formamide and acetanilide. Acid acridinium compounds of polybasic acids, the acid radicals of which contain metals, may be obtained, e.g. from 2,7-dimethyl-3,6-diamino-10-methyl acridinium - ketone compound and sodium ammonium hydrogen phosphate. In examples: (1) 3,6-diamino-10-methyl-acridinium-acetone compound is boiled with water and a little animal charcoal, and the acetone distilled in a current of nitrogen; the solution so obtained is treated with (2) sodium metavanadate to give 3,6-diamino-10-methylacridinium vanadate and (3) potassium chlorate to give 3,6-diamino-10-methylacridinium chlorate. Also in examples, 3,6-diamino-10-methylacridinium acetone compound is boiled with solutions of (4) quinic acid to give the quinate; (5) camphoric acid and caustic soda to give the sodium salt of the 3,6-diamino-10-methylacridinium camphoric acid compound; (6) microcosmic salt; (7) ammonium fluoride to give the fluoride; (8) 2-pyridone-5-arsinic acid; (9) acetamide to give the acetate; (10) 2,7-dimethyl-3,6-diamino-10-methylacridinium-acetone compound is heated with a solution of aniline hydrochloride, and the aniline and acetone distilled, giving the acridinium chloride; (11) 3,6-diamino-10-methylacridinium-cyclohexanone compound is boiled with p-oxybenzoic acid solution to give the p-oxybenzoate. The solution obtained as in (1) above is (12) treated with pyrocatechol to give the corresponding ether; (13) evaporated and treated with isoamylalcohol and methyl alcohol to give the isoamylether. In the Specification as open to inspection under Sect. 91, 3,6-diamino-10-allylacridinium acetone compound is converted to its tribromophenol ether, 3,6-diamino-10-oxyethylacridinium-cyclohexanone compound is converted to its pyrocatechol ether, 3,6-diamino-10-methylacridinium acetone compound is converted to its benzyl ether by boiling with benzyl alcohol without intermediate isolation of the acridinium hydroxide, 2,7-dimethyl-3,6-diamino-10-methylacridinium - acetone compound is heated with formic acid solution, and 3,6-diamino-10-methylacridinium hydroxide solution is heated with glutamic acid. This subject-matter does not appear in the Specification as accepted.

Title: Process for manufacture of alkylated 3,6-diamino acridinium compounds
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 344627, (12.03.1931); Patent Class.: C07D219/08
CODEN: BAXXDU

Abstract:
Alkylated 3,6-diaminoacridinium compounds are obtained by mixing 3,6-diaminoacridine with an alkylating agent and heating the mixture to 90-120 °C. Dialkyl sulphates or alkyl esters of aryl sulphonic acids may be used and an inorganic salt such as sodium chloride may be added, but no solvent is needed. The compounds appear to contain an alkyl substituent on the ring nitrogen atom and also on one of the amino groups; they have high bactericidal power and dye tanninmordanted cotton and leather orange shades. In an example the methyl ester of p-toluene sulphonic acid is employed as alkylating agent; the product gives the reactions of an acridinium compound and when diazotized, turns to claret-red and couples with azo-components, whereas the 3,6-diaminoacridine gives violet diazo compounds. It also differs from the 3,6-diaminomethylacridinium compound (produced by methylation and hydrolysis of the 3,6-diacetaminoacridine) which dyes tannin-mordanted cotton yellow shades. The Specification as open to inspection under Sect. 91 (3) (a) relates to the above alkylation treatment applied to an aminoacridine compound of the general formula wherein x indicates hydrogen or an acyl group, and contains additional examples in which 3,6-bisacetaminoacridine is alkylated with dimethyl- and diethyl-sulphate, or with the methyl ester of p-toluene-sulphonic acid in the presence and absence of sodium chloride; this subject-matter does not appear in the Specification as accepted.

Title: Manufacture of acridinium compounds
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 434497, (03.09.1935); Patent Class.: C07D219/08
CODEN: BAXXDU

Abstract:
New acridinium compounds are obtained by condensing a 3,6-diamino-10-alkyl or benzyl-acridinium compound with an aliphatic, hydroaromatic or aliphaticaromatic ketone in presence of caustic alkali. One of the amino groups reacts. The products are useful for the manufacture of pharmaceutical preparations. According to examples: (1) 3,6-diamino-10-methylacridinium chloride is condensed with acetone, or acetophenone; (2) the corresponding sulphate is condensed with cyclohexanone; (3) the corresponding 10-benzyl compound is condensed with acetone. Further specified acridinium-compounds include the bromide, and specified ketones include methylethyl ketone, diethylketone, methyl cyclohexanone, propiophenone, butyrophenone, tolylmethyl-ketone, methyl cyclohexanone and methyl propylketone. A sample has been furnished under Sect. 2 (5) of the product obtainable by condensing 2,7-dimethyl-3,6-diamino-10-methylacridinium chloride with acetone in alkaline solution. The Specification as open to inspection under Sect. 91 comprises also examples of the condensation of a 3,6-diamino-10-methylacridinium lactate and acetylacetone, and the use of salts such as the carbonate, bicarbonate, nitrate, tartrate, oxalate, glycollate, formate acetate and propionate of the acridinium compounds This subject-matter does not appear in the Specification as accepted.

Title: Process for the manufacture of acridinium compounds
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 450254, (13.07.1936); Patent Class.: C07D219/10, C07D219/12
CODEN: BAXXDU

Abstract:
10-Alkyl- or aralkylacridinium compounds substituted in the 9-position by an amino group containing a further basic radicle, are obtained (1) by replacing a reactive substituent in the 9-position with an aliphatic polyamine containing at least one primary or secondary amino group, (II) by first replacing the reactive substituent in 9-position by an amino alcohol or aminoalkylhalide group, and treating the product with a primary or secondary amine, the intermediately-formed hydroxyalkylamino compounds being esterified, if desired, prior to the reaction with amine, and (III) by ring-closing the amides of N-alkyl- or N-aralkyl-diarylamino-2-carboxylic acids substituted in the amide group by an aliphatic amine radicle. The basic radicle attached to the 9-amino group may contain one or more nitrogen atoms and may be substituted by OH-groups or interrupted by nitrogen or sulphur atoms. The acridine nucleus may be substituted by halogen, alkyl or alkoxy groups, and nitro and amino group. Specifications 267,169, [Class 2 (iii)], and 363,392 are referred to. According to examples (1) 9-chloro-10-methylacridinium chloride is treated with diethylaminoethylamine and converted to the quaternary hydrochloride; the methylene disalicyclic quaternary salt of the 9-a-diethylamino-d-pentylamino-10 methylacridinium compound may be obtained by the same method and precipitation from the hydrochloride; (2) 9-chloro-10-benzylacridinium chloride (obtained by treating 10-benzylacridone with PCl₅) is treated with a-diethylamino-d-amino-pentane, and converted to the quaternary citrate; (3) 6,9-dichloro-10-methylacridinium chloride, (obtained by treating 6-chloro-10-methylacridone with PCl₅) are treated with a-diethylamino-d-aminopentane, and converted to the methylenedisalicylic salt; (4) 2-methoxy-6,9-dichloro-10-methylacridinium, (obtained by treating 2-methoxy-6-chloro-10-methylacridone with PCl₅) is treated with a-diethylaminoethylamine to give the corresponding 9-substituted derivative; 2-methoxy-6-chloro-9-(a-diethylamino-b-hydroxy-g-propyl-amino)-10-methylacridinium chloride is obtained in a similar manner. Samples have been furnished under Sect. 2 (5) of the 1,1<1>-methylene-di(2-hydroxy-3-naphthoic acid salt of 4-nitro-9(b -diethylaminoethylamino)-10-methylacridinium obtained by the method of process (III) and by precipitation from the citric salt; the salt of 4-nitro-9(w-diethylaminoethyl-g-mercapto-propylamino-10-methyl-acridinium with the same methyleneoxynaphthoic acid is obtained in a similar manner from diethylaminoethyl-g-mercaptopropylamine, (prepared by treating bromopropylphthalimide with b- mercaptoethyldiethylamine and hydrolysis of the phthalic residue); the dihydrochloride salt of 2-methoxy-9(g -diethylamino-b- hydroxypropylamino-ethylamino) acridinium-10-methylchloride prepared by method I from the triamine g-diethylamino-b-hydroxy-propylamino - ethylamine, which may be obtained by treating 1-amino-3-diethylamino-2-propanol (cf. Specification 275,622, [Class 2 (iii)]), with bromethylphthalimide, followed by saponification of the product. The Specification as open to inspection under Sect. 91 refers to the use of basic radicles in which the aliphatic group may be interrupted also by oxygen. This subject-matter does not appear in the Specification as accepted.

Title: Manufacture of salts of acridinium bases
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 454375, (28.09.1936); Patent Class.: C07D219/06, C07D219/08, C07D219/10
CODEN: BAXXDU

Abstract:
Salts of acridinium bases are made by dissolving the bicarbonate of the base in the acid whose salt is required. The bicarbonate is made by treating a salt of the base such as the chloride, bromide, sulphate or nitrate with excess of the bicarbonate of sodium, potassium or lithium in cold or warm water or by treating with a caustic alkali or sodium carbonate and carbon dioxide. The alkyl-acridinium compounds may be substituted at the nitrogen atom by methyl, ethyl, propyl, b-hydroxypropyl or butyl radicles and in the nucleus by one or more amino, methyl, ethyl, propyl, methoxy or ethoxy groups. As carboxylic acids in which the bicarbonates may be dissolved to form the corresponding organic acid salts are mentioned formic, acetic, propionic, butyric, lactic, tartaric, benzoic, o-, m-, and p-toluic, glycollic, citric, gluconic, and quinic acids. Examples describe the manufacture of 3,6-diamino-10-methylacridinium acetate and lactate, 3,6-dimethoxy-10-methylacridinium acetate, 2-ethoxy-9-amino-10-methylacridinium acetate, lactate and tartrate, 3-methoxy-6-hydroxy-10-methylacridinium lactate, and 2,7-dimethyl-3,6-diamino-10-methylacridinium lactate, tartrate or acetate.

Inventor(s): A.G. Green and E.B. Adams
Title: Production of red basic dyestuffs
(British Dyestuffs Corp. Ltd.) Brit. Pat. Appl. GB 194165, (08.03.1923)
CODEN: BAXXDU

Abstract:
Dialkylamidoacridinium salts, more particularly the tetramethyldiamido-methylacridinium salts, are converted by bromination into other dyestuffs dyeing redder shades. On treatment with acids or acid salts the brominated products yield still other dyestuffs which dye or print in more bluish shades; the change also occurs during bromination if sufficient acid is present. Halogenated acridines such as those described in Specification 165,721 do not undergo this transformation unless first converted into acridinium salts by means of dimethylsulphate or the like. In examples, bromination products, and the transformation products thereof, from the following acridinium derivatives are described:- tetramethyldiamidomethylacridinium methyl sulphate, tetramethyldiamido-phenyl-methylacridinium methyl sulphate (made by action of dimethyl sulphate on Acridine Orange R), and the oxyethyl-acridinium chloride made by action of ethylene chlorhydrin on tetramethyl diaminoacridine; the transformation products are in each case isolated as double compounds with zinc chloride. The Provisional Specification refers also to the use of chlorine in place of bromine.

Inventor(s): S. Hata, K. Matsumura and K. Ishihara
Title: Method of preparing 9-amino-3,6-dimethoxy-10-methyl-acridinium chlorides
US Pat. Appl. US 2083908, (15.06.1937); Patent Class.: C07D219/10
CODEN: USXXDP
keywords: conversion of 3,6-Diaminoacridone into 3,6-Dihydroxyacridone (no diazotation, but hydrolysis with conc. sulfuric acid at 190 °C), 3,6-Dimethoxyacridone, 3,6-Dimethoxy-10-methylacridone, 3,6-Dimethoxy-N-methylacridone, 9-Chloro-3,6-dimethoxy-10-methylacridinium-chloride
Vergleiche Matsumura, K.: J. Am. Chem. Soc. 51, 1929, 816-820.

Inventor(s): R.W.E Stickings
Title: The manufacture of a soluble salt of 3,6-diamino-10-methyl-acridinium
(May & Baker Ltd.) Brit. Pat. Appl. GB 439902, (17.12.1935); Patent Class.: C07D219/08
CODEN: BAXXDU

Abstract:
3,6-Diamino-10-methyl-acridinium methane-sulphonate is prepared by interaction of the corresponding acridinium hydroxide or salt with methane-sulphonic acid or a salt thereof. The product, which is readily water-soluble, is useful therapeutically. Examples are given. Specifications 328,212, [Class 2 (iii)], and 345,631 are referred to.

Title: Process for obtaining coloured discharge effects
(Durand & Hugenin AIG) Brit. Pat. Appl. GB 361678, (26.11.1931); Patent Class.: D06P5/15C
CODEN: BAXXDU
keywords: Thiopyronine
Abstract:
Coloured discharge effects of enhanced intensity are obtained in the reduction method by employing printing pastes containing, in addition to the reducing agent, a chlorate as oxidizing agent. In examples (1) printing pastes for cotton contain (a) Chromorhodin BR, or BB or Modern yellow, tragacanth, hydrosulphite NF, chromium acetate and sodium chlorate, or (b) Thiopyronine or Rhodamine B extra, monoethylglycol, gum arabic, hydrosulphite NF, tannin and sodium chlorate; cotton dyed with a dischargeable dyestuff is printed with one of these pastes, dried, steamed and washed, the washing being preceded in the case of the pastes (b) by treatment in a tartar emetic solution; (2) printing pastes for wool contain (a) Rhodamine B extra, monoethylglycol, British gum, hydrosulphite NF and sodium chlorate, or (b) Fast acid violet A2R or Eosine blue No. 55, British gum, hydrosulphite NF and sodium chlorate; (3) printing pastes for silk contain (a) Thiopyronine, Rhodamine B extra, or Acridine red brown O (Specification 316,315, [Class 15 (ii), Dyeing, Processes &c. for]), monoethylglycol, gum arabic, hydrosulphite CW (sodium sulphoxylate containing zinc oxide), and sodium chlorate or (b) Thionine blue GO or Eosine blue No. 55, gum arabic, hydrosulphite CW and sodium chlorate, and (4) a printing paste for acetate silk contains Thionine blue GO, gum arabic, hydrosulphite NF and sodium chlorate; dyed wool, silk, or acetate silk respectively are printed with one of these pastes, dried, steamed, and washed.

Inventor(s): F. Mietzsch and H. Mauss
Title: Process for the manufacture of acridine derivatives
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 441007, (06.01.1936); Patent Class.: C07D219/04, C07D219/10, C07D219/12
CODEN: BAXXDU

Abstract:
Acridine derivatives are prepared by (1) reacting upon acridines containing in the 2-position a halogen atom or an alkyl group and in the 9-position as a reactive substituent halogen, aryloxy-, alkoxy-, mercapto-, substituted mercapto-, or sulpho- group, with a base or salt thereof containing at least two nitrogen atoms at least one of which is in a primary or secondary amino group; (2) reacting upon the acridines specified in (1) with a base or salt thereof containing at least two nitrogen atoms one of the amino groups being substituted by an acyl residue, the latter being subsequently split off by saponification; (3) reacting upon acridines specified in (1) with an amino alcohol or an amino substituted halogen alkyl compound and further reacting the product with ammonia or a primary or a secondary amine, if necessary after esterification of the hydroxyl group; (4) reacting upon acridine derivatives which differ from those specified in (1) by containing a nitro or amino group in 2-position, according to the processes of (1), (2) or (3) followed by reduction if necessary, diazotisation and a Sandmeyer replacement to convert the 2-nitro- or -amino- group to a 2-halogen substituent; (5) subjecting a diphenylamine-6-carboxylic acid amide basically substituted in the amide group and containing in the 4<1>-position a halogen atom or an alkyl group or a nitro- or acylamino group to ring closure to form the acridine derivative, a nitro- or acylamino group in 2-position then being respectively reduced or saponified, followed by diazotisation and a Sandmeyer replacement to give a 2-halogen derivative. The basic substituents are of the type defined in Specifications 363,392 and 437,953. In examples: (1) 2,9-dichloracridine (prepared from 4<1>-chlordiphenylamine-6-carboxylic acid by ring closure and chlorination) is condensed with a-diethylamino-d-aminopentane, a-diethylamino-b-hydroxy-g-aminopropane a-diethylamino-b-aminoethane, a-dimethylamino-g- aminopropane, a-diethylamino-d-aminobutane, a-diallylamino-b-aminoethane, a-diethylaminoethylthio-g-aminopropane, a- dimethylaminoethoxy-b-aminoethane and a-diethylamino-e-aminopentane; (2) 2-methyl-9-chloracridine (prepared from 4<1>-methyldiphenylamine-6-carboxylic acid by ring closure and chlorination) is condensed with a-diethylamino-d -aminopentane; 2-ethyl-9-chloracridine (prepared analogously to the 2-methyl derivative) may be used instead; (3) 2-bromo-9-chloracridine (prepared from 4<1>-bromdiphenylamine-6-carboxylic acid by chlorinating agents) is condensed with a-diethylamino-d-aminopentane; 2-iodo-9-chloracridine (prepared analogously to the 2-bromo derivative) may be used instead or condensed with a-diethylamino-g-aminobutane or a triamine of the formula. Samples have been furnished under Sect. 2 (5) of (a) 2-chloro-9-(p-aminomethylphenylamino)-acridine prepared by reacting 2,9-dichloracridine with phenol and the resulting 9-phenoxy derivative with N-(4-aminobenzyl)acetamide followed by saponification in aqueous hydrochloric acid; (b) 2-chloro-9-(p-diethylaminoethyloxyphenylamino)-acridine prepared by condensing 2-chloro-9-phenoxyacridine with 4-aminophenylhydroxyethylether, and boiling the product with thionyl chloride and diethylamine; (c) 2-chloro-9-(a-piperido-g -propylamino)-acridine prepared from 2-nitro-9-chloracridine (obtained by ring closure of 4<1>-nitrodiphenylamine-6-carboxylic acid and chlorination) by condensation with g-piperido-a-propylamine, reduction by means of iron in acetic acid, diazotisation and a Sandmeyer replacement with cuprous chloride; (d) 2-chloro-9-(p-diethylaminoethylmercaptophenylamino)-acridine prepared by treating 4-chlordiphenylamine-6-carboxylic acid with phosphorus pentachloride and condensing with 4-aminophenyldiethylaminoethylthioether (cf. Specification 437,953) and the product ring-closed by heating with phosphorus oxychloride. Most of these products are isolated in the form of their salts with acids. Specification 267,169, [Class 2 (iii)], also is referred to. a-Diethylaminoethylthio-g-aminopropane is prepared by reacting diethylaminoethylmercaptan with bromopropylphthalimide and saponifying. The triamine of the above formula is prepared by reacting monoethylamine with diethylaminoepihydrin, the product with epichlorhydrin, and finally with ammonia. N-(4-aminobenzyl)-acetamide is prepared by reduction of the corresponding 4-nitro derivative with iron and acetic acid. 4-Aminophenyl-hydroxyethylether prepared by reacting 4-nitrophenol with chlorethyl alcohol and reducing with iron in acetic acid. g-Piperido-a-propylamine is prepared by reacting bromopropylphthalimide with piperidine and saponifying.

Title: Process for the manufacture of stable acridine salt solutions
(IG Farbenindustrie AG) Brit. Pat. Appl. GB 395405, (17.07.1933); Patent Class.: C07D219/08
CODEN: BAXXDU

Abstract:
Aqueous solutions for injection purposes are manufactured by incorporating a reducing substance, other than a carbohydrate, with a salt or solution of a salt of an aminoacridine or aminoacridinium compound other than the salts of 3,6-diaminoacridine or 3,6-diamino-10-alkylacridinium or double compounds thereof. Suitable acridine compounds are the salts of substitution products of 3,6-diaminoacridine and 3,6-diamino-10-alkylacridinium compounds and of other aminoacridines or acridinium compounds or their substitution products or the corresponding double compounds. As reducing substances may be employed the salts of sulphurous, hydrosulphurous or sulphoxylic acids, as such or in the form of derivatives, e.g. compounds with aldehydes or ketones, also hydrazines and hydroxylamines, or mixtures thereof. Compounds advantageous for therapeutical application, e.g. glucose, adrenaline, acid amides, glycerine, pyridine, methylene blue, calcium chloride or silver salts, may also be added. Examples describe the preparation of solutions containing: (1) 2,7-dimethyl-3,6-diamino-10-methylacridinium chloride, 2,7-dimethyl-3,6-diaminoacridine hydrochloride, sodium bisulphite and sodium sulphite; (2) 2,7,9-trimethyl-3,6-diamino-10-methylacridinium chloride, acetone bisulphite and glucose; (3) 2,7,9-trimethyl-3,6-diaminoacridine hydrochloride, phenylhydrazine acetate and glucose (to render the solution isotonic to blood); (4) 2-methyl-3-amino-6-dimethylamino-10- methylacridinium sulphomethylate (obtainable by condensation of formic acid with N-dimethyl-m-phenylenediamine and 4-methyl-1,3-phenylenediamine and subsequent alkylation with methyl sulphate) and sodium sulphite, with or without silver sulphate, methylene blue or pyridine; (5) 2,7-dimethyl-3-amino-6-dimethylamino-10-methylacridinium chloride, acetone bisulphite, sodium sulphite and glucose or an acid amide; (6) 2,7-dimethyl-3,6-tetramethyldiamino-10-methylacridinium chloride (obtainable by condensation of formic acid with 4-methyl-3-N-dimethylaminoaniline, alkylation with methyl sulphate and saponification with hydrochloric acid), hydroxylamine and sodium hydrosulphite; (7) 2,7-dimethyl-3-amino-6-dimethylamino-10-methylacridinium chloride, sodium bisulphite and sodium sulphite. The Specification as open to inspection under Sect. 91 describes also the preparation of tablets by mixing the substances employed in (7) with ureas, sugars or other water soluble admixtures. This subject-matter does not appear in the Specification as accepted. ALSO: Aqueous solutions for injection purposes are manufactured by incorporating a reducing substance, other than a carbohydrate, with a salt or solution of a salt of an aminoacridine or aminoacridinium compound other than the salts of 3,6-diaminoacridine or 3,6-diamino-10-alkylacridinium or double compounds thereof. Suitable acridine compounds are the salts of substitution products of 3,6-diaminoacridine and 3,6-diamino-10-alkylacridinium compounds and of other aminoacridines or aminoacridinium compounds or their substitution products or the corresponding double compounds. As reducing substances may be employed the salts of sulphurous, hydrosulphurous or sulphoxylic acids, as such or in the form of derivatives, e.g. compounds with aldehydes or ketones, also hydrazines and hydroxylamines, or mixtures thereof. Compounds advantageous for therapeutic application, e.g. glucose, adrenaline, acid amides, glycerine, pyridine, methylene blue, calcium chloride or silver salts, may also be added. Examples describe the preparation of solutions containing: (1) 2,7-dimethyl-3,6-diamino-10-methylacridinium chloride, 2,7-dimethyl-3,6-diaminoacridine hydrochloride, sodium bisulphite and sodium sulphite; (2) 2,7,9-trimethyl-3,6-diamino-10-methylacridinium chloride, acetone bisulphite and glucose; (3) 2,7,9-trimethyl-3,6-diaminoacridine hydrochloride, phenylhydrazine acetate and glucose (to render the solution isotonic to blood); (4) 2-methyl-3-amino-6-dimethylamino - 10-methylacridinium sulphomethylate and sodium sulphite, with or without silver sulphate, methylene blue or pyridine; (5) 2,7-dimethyl-3-amino-6-dimethyl-amino-10-methylacridinium chloride, acetone bisulphite, sodium sulphite and glucose or an acid amide; (6) 2,7-dimethyl-3,6-tetra-methyldiamino-10-methylacridinium chloride, hydroxylamine and sodium hydrosulphite; (7) 2,7-dimethyl-3-amino-6-dimethylamino-10-methylacridinium chloride, sodium bisulphite and sodium sulphite. The Specification as open to inspection under Sect. 91 describes also the preparation of tablets by mixing the substances employed in (7) with ureas, sugars or other water-soluble admixtures. This subject-matter does not appear in the Specification as accepted.

Inventor(s): Morgan. E.N. and D.J. Tivey
Title: Process for producing acridine compounds
(Parke Davis & Co.) Brit. Pat. Appl. GB 789696, (20.01.1958); Patent Class.: C07D219/02, C07D219/04, C07D219/06
CODEN: BAXXDU
keywords: 9-Methylacridine from 9-Chloroacridine and malonic acid diethylesters, reaction of 9-Chloroacridine with malono dinitrile
Abstract:
9-Methyl acridines and their addition salts having in the free base form the general formula are obtained by reacting a 9-haloacridine of formula with a malonic acid derivative M-CH(Y)Z in the presence of an anhydrous organic solvent at a temperature above 50 °C to obtain an acridyl-9-malonic acid derivative of formula the latter derivative is then subjected to direct hydrolysis at a temperature of at least 75 °C in the presence of an aqueous mineral acid or to stepwise hydrolysis firstly in an aqueous basic medium at a temperature in the range 90-150 °C and then in the presence of aqueous mineral acid at a temperature above 75 °C, M being an alkyl metal, R1 and R2 being the same or different and representing hydrogen, lower alkyl, lower alkoxy or halogen radicals, X being a chlorine or bromine radical and Y and Z being the same or different and representing nitrile or lower alkoxy-carbonyl groups. Lower alkyl and alkoxy groups are those containing not more than 4 carbon atoms. Suitable solvents for the reaction between the 9-haloacridine and the malonic acid derivative are, for example, lower aliphatic alcohols, cyclic ethers such as dioxane, aromatic hydrocarbons such as benzene and toluene, and petroleum ether. In the examples: (a) a solution of 9-chloroacridine in toluene is added to diethyl sodio-malonate and the mixture is heated; hydrochloric acid is added and 9-methyl acridine hydrochloride crystallizes out; the pure base is obtained by treating the hydrochloride with ammonia; (b) 9-chloracridine is added to a solution of diethyl sodio-malonate and the mixture is heated and treated with hydrochloric acid; the hydrochloride formed is treated with caustic soda to give diethyl acridyl-9-malonate, which on treatment with hydrochloric acid gives 9-methyl acridine hydrochloride; (c) a mixture of 9-chloroacridine and benzene is added to a solution of sodium ethoxide and malononitrile in ethanol and the resulting mixture is heated; on acidification dicyano methyl acridine is obtained; on treating with sulphuric acid 9-methylacridine sulphate is obtained and this gives the free base on treatment with ammonia; (d) 2,9-dichloroacridine is added to a solution of sodium and ethyl malonate in ethanol; toluene is added and the mixture is heated; the resulting mixture is heated with hydrochloric acid to give 2-chloro-9-methylacridine hydrochloride; (e) 3,6,9-trichloroacridine is added to a solution of sodium and ethyl malonate in ethanol and the mixture is heated, hydrochloric acid is added and the precipitate formed is treated with ammonia to give 3,6-dichloro-9-methylacridine; (f) 9-chloroacridine is treated with ethyl cyano acetate and sodium ethoxide in a mixture of benzene and ethanol to give ethyl acridyl-9-cyanoacetate; on treating with sodium carbonate solution 9-cyanomethyl acridine is obtained and this on treatment with hydrobromic acid followed by treatment with ammonia gives 9-methyl acridine; (g) 2-methoxy-6,9-dichloroacridine is dissolved in toluene and added to a mixture of sodium, ethyl malonate and ethanol to give diethyl-2-methoxy-6-chloroacridyl-9-malonate hydrochloride; on hydrolysis with hydrochloric acid and subsequent treatment with ammonia 2- methoxy-6-methyl-9-chloroacridine is obtained; and (h) 3-methyl-9-chloroacridine is added to diethyl sodio-malonate, the mixture is heated and hydrochloric acid is added; 3,9-dimethylacridine hydrochloride is obtained and on treatment with ammonia it gives the free base.

Inventor(s): K. William and A.A. Goldberg
Title: Process for the production of acridine derivatives bearing cyano substituents
(Ward Blenkinsop & Co. Ltd.) Brit. Pat. Appl. GB 600354, (07.04.1948); Patent Class.: C07D219/02, C07D219/04, C07D219/06, C07D219/08
CODEN: BAXXDU
keywords: 9-Chloroacridine, reaction of 9-Chloroacridine with malodinitrile, malonodinitrile, malonic acid dinitrile
Abstract:
Meso-substituted acridines having the general formula are obtained by treating a meso-halogenated acridine, in the presence of an alkali metal or of an alkali metal hydroxide, with a cyano compound having the general formula NCCH2X in which X represents a negative group such that the cyano compound is capable of forming an alkali metal derivative by replacement of a hydrogen atom of the methylene group with an alkali metal. Advantageously, there is present a substantially molecular proportion of alkali metal or its alkoxide with respect to the cyano compound. Specified cyano compounds: cyano acetic esters, e.g. of a lower or higher alcohol, e.g. methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, lauryl, oleyl, linoleyl, palmityl or stearyl alcohols. An aralkyl, e.g. a benzyl, ester, may be used. X may also represent: a group having the formula -COR3 wherein R3 represents an alkyl or aryl group, e.g. a methyl, ethyl, phenyl group; an aralkyl, e.g. a benzyl, radical which may contain one or more additional substituents in the benzene ring; or a nitrile. The meso-halogenated acridines may contain one or more of the following nuclear substituents by p alkyl (e.g. methyl or ethyl), alkoxy (e.g. methoxy or ethoxy), nitro, amino, substituted amino, cyano and halogen in either or both of the benzenoid nuclei, e.g. 2-methoxy-9-chloro-acridine, 2-methoxy-6,9-dibromoacridine. Specified reaction solvents are: anhydrous alcohol, benzene, toluene, xylene or dioxane. Specified alkali metals include potassium and lithium. In examples: (1) 9-chloroacridine is refluxed with a mixture of sodium and ethyl cyanoacetate in anhydrous ethyl alcohol to obtain ethyl (acridyl-9)-cyanoacetate; (2) to (8) there are refluxed, in ethyl alcohol mixtures of: (2) phenyl acetonitrile, sodium and 9-chloroacridine to obtain phenyl-(acridyl-9-acetonitrile, yielding phenyl-(acridyl-9)-acetonitrile; (3) malodinitrile, sodium and 9-chloro-acridine, yielding (acridyl-9)-malonodinitrile; (4) ethylcyanoacetate, sodium ethoxide, dioxane, 2-methoxy-9-chloro-6- cyano-acridine yielding ethyl-(2-methoxy-6-cyanoacridyl-9)- cyanoacetate; (5) ethyl cyanoacetate, sodium ethoxide, 3-cyano-9-chloro-acridine, yielding ethyl-(3-cyanoacridyl-9)-cyanoacetate; (6) 2-cyano-9-chloroacridine, sodio cyanoacetic ester, yielding ethyl-(2-cyano-acridyl-9)- cyanoacetate; (7) sodio-ethylcyanoacetate, benzene, 2-dimethylamino-6,9-dichloroacridine yielding ethyl-(2-dimethylamino-6-chloro-acridyl-9)-cyanoacetate; (8) as in (7) using 2-methoxy-6,9-dichloroacridine as the acridine starting material.

Inventor(s): L. Katz
Title: Bactericidal and fungicidal compounds
(Schenley Ind. Inc.) US Pat. Appl. US 2767173, (16.10.1956); Patent Class.: C07C323/62, C07D215/12
CODEN: USXXDP
keywords: 4-Chlorothiosalicylic acid, 5-Chlorothiosalicylic acid, 3,5-Dichlorothiosalicylic acid, 5-Bromthiosalicylic acid, 3,5-Dibromothiosalicylic acid, 4-Methoxysulfonylthiosalicylic acid, 4-Methoxythiosalicylic acid, 4-Methoxy-2-mercaptobenzoic acid, 4-Chloro-2-mercaptobenzoic acid, 4-Methoxyanthranilic acid, 4-Methoxy-2-aminobenzoic acid
vgl. Katz, L.; Karger, L.S.; Schroeder, W.; Cohen, M.S.: J. Org. Chem. 18, 1953, 1380-1402.

Inventor(s): D.C. Neckers and J. Shi
Title: Fluorone and pyronin Y derivatives
(Spectra Group Ltd. Inc.) Eur. Pat. Appl. EP 0515133, (25.11.1992); Patent Class.: C07D311/82 ; C07D311/84 ; G01M3/20 ; G01T1/06 ; G03F7/031
Klassifikationssymbol (EC) : G03F7/031, C07D311/82, C07D311/84, C07D498/06
CODEN: EPXXDW
keywords: Pyronine Y, Pyronine G, cyclisation of 2,2',4,4'-Tetrahydroxybenzophenone forming 3,6-Dihydroxyxanthone, 3,6-Dihydroxy-9-xanthone
Abstract:
A novel class of compounds is described, certain members of which are useful as fluorescers or as photoinitiators. The compounds have the general structures (I) (II) (III) or (IV): where A is selected from hydrogen, alkyl, aryl, alkenyl, alkynyl, dichlorotriazinylamino, and electron withdrawing groups (EWG) which are stronger electron withdrawing groups than a phenyl group or a halogen-substituted or a carboxyl-substituted phenyl group; X is oxygen, sulfur, selenium, tellurium or >C=0 and preferably oxygen; Z is a counter ion; R is hydrogen, alkyl, aryl or aralkyl; R<1><1>-R<1><6> are the same or different and represent a hydrogen atom or a halogen atom; and R<1><7> is a hydrogen atom or a group of the formula -OR'. The compounds of formula (I) and (II) may be substituted or unsubstituted at the 2, 4, 5 and 7 positions. When the 2, 4, 5 and 7 positions are unsubstituted, A cannot be hydrogen or methyl.

Inventor(s): Peter Zimmer
Title: Method for producting 3,6-Diaminoacridine or its hydrochloride
(Zimmer, Peter) PTC Pat. Appl. WO 9907683, (18.02.1999); Patent Class.: C07D219/08 ; C09B15/00
Klassifikationssymbol (EC) : C09B15/00, C07D219/08
CODEN: PIXXD2

Abstract:
The invention relates to a novel process for producing 3,6-diaminoacridine or its hydrochloride. The inventive processes enable these substances to be produced with a high degree of purity.

Inventor(s): V.N. Glushko, I.L. Parbuzina and G.S. Petrova
Title: Method of preparing 3,6-Bis(dimethylamino)-acridine-hydrochloride as acridine-hydrochloride orange chlorohydrate dyeining agent
(Glushko, V.N.; Parbuzina, I.L.; Petrova, G.S.) USSR Pat. Appl. SU 694525, (30.10.1979); Patent Class.: C09B15/00
CODEN: URXXAF
keywords: 3,6-Bis(dimethylamino)-acridine-hydrochlorid

Author(s): E.G. Davis and S. Smiles
Title: New syntheses of thioxanthone and its derivatives
J. Chem. Soc. Trans. Vol. 97, p. 1290-1299 (1910); ISSN: 0368-1645; CODEN: JCHTA3

keywords: Treatment of thiosalicyclic acid and aromatic compounds with cold sulfuric acid; formation of 3-Methoxythioxanthone from thiosalicylic acid and anisole; 3-Methoxythioxanth-9-one; 2-Mercaptobenzoic acid
New syntheses of Thioxanthone and its derivatives by Smiles, S.: Proc. Chem. Soc. 26, 1910, 342.

Author(s): M. Protiva, K. Sindelár, Z. Sedivy and J. Metysova
Title: Potential metabolites of tricyclic neuroleptics and their fluorinated analouges; 3-Hydroxy-, 3-methoxy and 3-Fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin
Collect. Czech. Chem. Commun. Vol. 44, p. 2108-2123 (1979); ISSN: 0366-547X; CODEN: CCCCAK

keywords: 4-Methoxy-2-iodobenzoic acid; 4-Methoxy-2-(phenylthio)benzoic acid

Author(s): K. Sindelár, J.O. Jilek, J. Metysová, J. Pomykácek and M. Protiva
Title: Potential metabolites of Clorotepin: 2- and 3-hydroxy derivatives of 8-Chloro-10(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin and their methyl ethers
Collect. Czech. Chem. Commun. Vol. 39, p. 3548-3559 (1974); ISSN: 0366-547X; CODEN: CCCCAK

keywords: 4-Methoxy-2-iodobenzoic acid; 2-Iodo-4-methoxybenzoic acid; diazotation of 2-Amino-4-methoxybenzoic acid; 4-Methoxyanthranilic acid

Author(s): A.H.A. Tinnemans, B. den Ouden, H.J.T. Bos and A. Mackor
Title: Photochemical conversion of norbornadiene into quadricyclane in the presence of acridone-type sensitizers
Recl. Trav. Chim. Pays-Bas Vol. 104, No. 4, p. 109-116 (1985); ISSN: 0165-0513; CODEN: RTCPA3

keywords: 3,6-Bis(dimethylamino)-10-methylacridone; Michler's Ketone; 4,4'-Bis(dimethylamino)benzophenone; longest wavelength absorption maximum
Abstract:
In this study, a series of acridinones and benzo-fused acridinones have been used for the first time as efficient photosensitizers for the norbornadiene-quadricyclane isomerization by near UV and visible iradiation. Their triplet energies (240-280 kJ Mol^-1) are well below the value of 290 kJ Mol^-1 which is generally assumed for norbornadiene. A mechanism is postulated involving an exciplex between sensitizer and norbornadiene. Limiting quantum yields of 0.5 and higher have been determined for this valence isomerization extrapolated to infinite norbornadiene concentration. Exciplex formation is supported by measurements of the rate of constant k₂ for quenching of excited sensitizer by norbornadiene, yielding values which are much smaller than the diffusion-controlled quenching constant.

Author(s): A. Yamagishi, T. Masui and F. Watanabe
Title: Selective activation of reactant molecules by reversed micelles
J. Phys. Chem. Vol. 85, p. 281-285 (1981); ISSN: 0022-3654; CODEN: JPCHAX

keywords: 3,6-Bis(dimethylamino)-acridone through oxidation of 3,6-Bis(dimethylamino)-acridinium-chloride with cerium(VI)-sulfate

Author(s): S. Jockusch, H.-J. Timpe, W. Schnabel and N.J. Turro
Title: Photoinduced energy and electron transfer between ketone triplets and organic dyes
J. Phys. Chem. A Vol. 101A, p. 440-445 (1997); ISSN: 1089-5639; CODEN: JPCAFH

keywords: Methylene blue; Thiopyronine; 3,6-Bis(dimethylamino)thioxanthylium-chloride; ATX; absorption maximum

Author(s): B. Aleksiev and M. Milosev
Title: Darstellung neuer Indandion-Analoga. 2. Mitteilung zur Darstellung neuer Indandion-Analoga
Pharmazie Vol. 24, No. 5, p. 291-292 (1969); ISSN: 0031-7144; CODEN: PHARAT

keywords: condensation of Diphen acid anhydride with methylpydridines and methylquinolines resulting in the formation of deeply coloured compounds
Abstract:
2-substituted analogues of 1,3-Indandiones were prepared from the condensation reaction between diphen acid anhydride and 2-methylquinoline or 2-methylpyridine and zinc chloride as catalystor.

Author(s): B. Aleksiev and M. Milosev
Title: Notiz über die Umsetzung von 9-Methylacridin mit Dicarbonsäureanhydriden. 3. Mitteilung zur Darstellung neuer Indandion-Analoga
Chem. Ber. Vol. 102, p. 2869-2872 (1969); ISSN: 0009-2940; CODEN: CHBEAM

keywords: condensation of phthalic acid anhydride with 9-Methylacridine on treatment with acetic anhydride-triethylamine; rearrangement of the obtained condensation products forming 2-substituted 1,3-Indandiones; Indan-2-(9-acridinyl)-1,3-dione; 2-(9-Acridinyl)-indandione-1,3; 2-(9-Acridinyl)-1,3-indandione
Abstract:
2-substituted 1,3-Indandiones were prepared from the condensation reaction between phthalic acid anhydride and 9-methylacridine in the precence of acetic anhydride and triethylamine. The intermediate 9-acridinylmethylene phthalide was rearranged under the influence of sodium methoxide to 2-(9-acridinyl)-1,3-indandione. In a similar reaction between pyridine-2,3-dicarboxylic acid anhydride (chinolinic acid anhydride) and 9-methylacridine, followed by sodium methoxide treatment, there was obtained 6-(9-acridinyl)-1-pyrindine-5,7-dione.

Author(s): O. Dimroth and R. Crigee
Title: Über einige meso-substituierte Dihydroacridine and ihre Dehydrierungsprodukte
Chem. Ber. Vol. 90, p. 2207-2215 (1957); ISSN: 0009-2940; CODEN: CHBEAM

keywords: addition reaction of methylene active compounds on acridinium salts; addition reaction of malonic acid dimethylester on N-methyl-2,7-dimethylacridinium-iodide; formation of 2,7-Dimethylacridine; dehydration of the addition reaction products on treatment with lead(IV)acetate

Author(s): F. Kröhnke and H.L. Honig
Title: Über Pseudobasen, V. Versuche in der Acridinium-reihe
Chem. Ber. Vol. 90, p. 2215-2225 (1957); ISSN: 0009-2940; CODEN: CHBEAM

keywords: addition reaction of methylene active compounds on acridinium salts; addition reaction of malonic acid dimethylester on N-methyl-acridinium-iodide; dehydration of the addition reaction products on treatment with lead(IV)acetate or air

Author(s): F. Kröhnke and H.L. Honig
Title: Notiz zur Kennnis der Acridiniumsalze
Chem. Ber. Vol. 90, p. 2226-2227 (1957); ISSN: 0009-2940; CODEN: CHBEAM

keywords: alkylation of acridine with allylbromide, benzylbromide; N-allyl acrididinium-bromide, N-benzyl acridinium-bromide

Author(s): F. Kröhnke and I. Vogt
Title: Über Pseudobasen, VI. meta-Substituionen im Chinolin- and Isochinolinkern von Pseudobasen-Addukten
Chem. Ber. Vol. 90, p. 2227-2236 (1957); ISSN: 0009-2940; CODEN: CHBEAM

Author(s): F. Kröhnke and H.L. Honig
Title: Additionen aktiver Methylenverbindungen an Acridin
Justus Liebigs Ann. Chem. Vol. 624, p. 97-108 (1959); ISSN: 0075-4617; CODEN: JLACBF

keywords: Addition methylenaktiver Verbindungen an Acridiniumsalze; Addition von Malonsäuredimethylester Acridin; Malodinitril; Malonodinitril; Malonsäuredinitril; Dimedon; Dehydrierung der Additionsprodukte durch Blei(IV)acetat and Sauerstoff; Luft; Nitromethan; 1,3-Indandione; 2-(9-Acridyl)-1,3-indandione; Indan-2-(9-acridyl)-1,3-dione; 2-(9-Acridyl)-indandione-1,3

Author(s): T.R. Kim, D.I. Chung and S.Y. Pyun
Title: Synthetic studies on the nucleophilic adducts of thiophenol derivatives to 4'-[[N-(9-acridinyl)]-1'-(n-methanesulfonyl)-3'-methoxyquinonediimide
J. Korean Chem. Soc. Vol. 40, No. 8, p. 565-570 (1996); ISSN: 1017-2548; CODEN: JKCSEZ

keywords: formation of 9-chloroacridine on treatment of acridone with thionyl chloride

Author(s): C. Graebe and K. Lagodzinski
Title: Über Acridon
Justus Liebigs Ann. Chem. Vol. 276, p. 35-53 (1893); ISSN: 0075-4617; CODEN: JLACBF

keywords: acridine; N-Methylacridinium-iodide; N-methylacridone

Author(s): I. Goldberg
Title: Über Phenylierungen bei Gegenwart von Kupfer als Katalysator
Ber. dtsch. Chem. Ges. Vol. 39, p. 1691-1692 (1906); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Umsetzung von Anthranilsäure and Brombenzol zu N-Phenylanthranilsäure; 2-Aminobenzoesäure; zu 2-(Aminophenyl)benzoesäure

Author(s): H. Jensen and F. Rethwisch
Title: Researches on Acridines. IV. The preparation of hydroxyacridines and different 5-positions acridine derivatives
J. Am. Chem. Soc. Vol. 50, p. 1144-1150 (1928); ISSN: 0002-7863; CODEN: JACSAT

keywords: Kondensation von o-Aminobenzaldehyd mit Brombenzolen zu 9-substituierten Acridinen; o-Aminoacetophenon zu 9-Methylacridin; o-Aminobenzophenon zu 9-Phenylacridin; 9-Acridincarbonsäuremethylester; Acridin-9-carbonsäure; 9-Methylacridin

Author(s): C.F.H. Allen and G.H.W. McKee
Title: Acridone
Org. Synth. Coll. Vol. Vol. II, p. 15-17

keywords: Herstellung von Acridon aus o-Chlorbenzoesäure and Anilin; 2-(Aminophenyl)benzoesäure

Author(s): A. Albert and B. Ritchie
Title: 9-Aminoacridine
Org. Synth. Vol. 22, p. 5-8 (1942);

keywords: Umsetzung von 2-(Aminophenyl)benzoesäure zu 9-Chloracridin mit Phosphorylchlorid; Chlorierung von Acridon zu 9-Chloracridin; Umsetzung von 9-Chloracridin mit Ammoniumcarbonat

Author(s): E. Bergmann and O. Blum-Bergmann
Title: Zwei isomere ms-Tetrahydro-9,9'-biacridyle (Bemerkungen zu der gleichnamigen Arbeit von K. Lehmstedt
Ber. dtsch. Chem. Ges. Vol. 63, p. 757-762 (1930); ISSN: 0365-9496; CODEN: BDCGAS

keywords: methylation of acridine zu N-Methylacridinium iodide with iodomethane; oxidation von 10-methylacridinium iodide to 10-methylacridone

Author(s): K. Lehmstedt and H. Hundertmark
Title: Die Nitrierung des N-Methylacridons and die Herstellung des 2,7-Diamino-10-mehylacridiniumchlorides
Ber. dtsch. Chem. Ges. Vol. 64, p. 2386-2394 (1931); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Umsetzung von Acridon zu N-Methylacridon mit Dimethylsulfat; Oxidation von 10-Methylacridiniumiodid zu 10-Methylacridon; Nitrierung von N-Methylacridon; 2,7-Dinitro-10-methylacridon; 2,7-Diamino-10-methylacridon; 2,7-Diamino-10-methylacridiniumchlorid

Author(s): K. Gleu, S. Nitsche and A. Schubert
Title: Die Einwirkung vom Phosphoroxychlorid and Oxalylchlorid auf Acridone
Ber. dtsch. Chem. Ges. Vol. 72, p. 1093-1099 (1939); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Additionsverbindungen von Phosphorylchlorid and Acridonen; Überführung von Acridonen in 9-Chloracridine durch die Einwirkung von Oxalylchlorid

Author(s): H. Decker
Title: Über die Einwirkung von Alkalien auf Jodalkylate der Chinolin- and Acridinreihe
J. Prakt. Chem. Vol. 153 [45, Ser. 2], p. 161-200 (1892); ISSN: 0021-8383; CODEN: JPCEAO

keywords: Methylierung von Acridin mit Iodmethan; Oxidation von 10-Methylacridiniumiodid zu 10-Methylacridon

Author(s): P. Ehrlich and L. Benda
Title: Über die Einwirkung von Cyankalium auf Pyronin- and Acridinium-Farbstoffe
Ber. dtsch. Chem. Ges. Vol. 46, p. 1931-1951 (1913); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Pyronine Y; Pyronine G; 3,6-Bis(dimethylamino)-xanthone; 3,6-Bis(dimethylamino)-xanth-9-one; 3,6-Bis(dimethylamino)-10-methylacridinium-salt; 3,6-Bis(dimethylamino)-10-methylacridone; 3,6-Diamino-10-methylacridinium-salt; 3,6-Diamino-10-methylacridone; 3,6-Bis(dimethylamino)-N-methylacridinium-salt; 3,6-Bis(dimethylamino)-N-methylacridone; 3,6-Diamino-N-methylacridinium-salt; 3,6-Diamino-N-methylacridone; Acridone; N-Methylacridone

Author(s): H. Gilman and S.M. Spatz
Title: Orientation in the metalation of amines
J. Org. Chem. Vol. 17, p. 860-864 (1952); ISSN: 0022-3263; CODEN: JOCEAH

keywords: N-Methylacridon aus N-Methyldiphenylamin and Kohlendioxid durch o-Metallierung mit Lithiumbasen

Author(s): D.C.R. Jones and F.A. Mason
Title: Some derivatives of 4,4'-Tetramethyldiamidodiphenylmethane
J. Chem. Soc., p. 1190-1192 (1934); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Sulfurierung /Sulfonierung von 4,4'-Bis(dimethylamino)diphenylmethan zu 4,4'-Bis(dimethylamino)diphenylmethan-2,2'-disulfonsäure mit Chlorsulfonsäure; Oxidierung von 4,4'-Bis(dimethylamino)diphenylmethan während der Einwirkung von verdünnter Salpetersäure; 2-Chlor-4,4'-bis(dimethylamino)diphenylmethan; 2,2'-Dichlor-4,4'-bis(dimethylamino)diphenylmethan; 3,3'-Dichlor-4,4'-bis(dimethylamino)diphenylmethan; 2-Brom-4,4'-bis(dimethylamino)diphenylmethan; 2,2'-Dibrom-4,4'-bis(dimethylamino)diphenylmethan; 3,3'-Dibrom-4,4'-bis(dimethylamino)diphenylmethan, 3,3'-Diaminodiphenylmethan; Methylierung von 3,3'-Diaminodiphenylmethan; Diazotierung von 4,4'-Bis(dimethylamino)diphenylmethan-2,2'-diamin; 2,2'-Diamino-4,4'-bis(dimethylamino)diphenylmethan; 2,2'-Bis(diazo)-4,4'-bis(dimethylamino)diphenylmethan; Chlorierung von 4,4'-Bis(dimethylamino)diphenylmethan; Bromierung von 4,4'-Bis(dimethylamino)diphenylmethan
Vergleiche DRP DE 65017, DRP DE 65739, DRP DE 88085, sowie DRP DE 54621

Title: Verfahren zur Darstellung alkaliechter blauvioletter Triphenylmethanfarbstoffe aus der Monosulfosäure des Tetramethyldiaminodiphenylmethans
(Joh. Rud. Geigy & Co., Basel, Schweiz) Dtsch. Reichspat. DE 88085, (23.07.1896); Patent Class.: C09B11/16

keywords: Sulfurierung /Sulfonierung von 4,4'-Bis(dimethylamino)diphenylmethan zu 4,4'-Bis(dimethylamino)diphenylmethan-2,2'-disulfonsäure, 4,4'-Bis(dimethylamino)diphenylmethan-2-sulfonsäure, 3,6-Bis(dimethylamino)-thioxanthen-10,10-dioxid
Vergleiche DRP DE 65017, DRP DE 54621, DRP DE 65739, sowie Jones, D.C.R.; Mason, F.A.: J. Chem. Soc. 1934, 1190-1192.

Author(s): J.C. Bardhan
Title: Studies in the Sterol-Oestrone group. Part 1. A synthesis of 3'-Keto-3,4-dihydro-1,2-cyclopentenophenanthrene
J. Chem. Soc., p. 1848-1851 (1936); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Kondensation von Acetessigsäuremethylester mit Bernsteinsäurehalbester-halbchlorid; 2-Ketohexandicarbonsäuredimethylester; b-Ketoadipinsäuredimethylester; b-Ketoadipinsäuremethylethylester; Succhinylchlorid-halbester

Author(s): L. Katz, L.S. Karger, W. Schroeder and M.S. Cohen
Title: Hydrazine derivatives. I. Benzalthio- and Bisbenzaldithio-salicylhydrazides
J. Org. Chem. Vol. 18, No. 10, p. 1380-1402 (1953); ISSN: 0022-3263; CODEN: JOCEAH

keywords: 4-Chlorthiosalicylsäure; 5-Chlorthiosalicylsäure; 3,5-Dichlorthiosalicylsäure; 5-Bromthiosalicylsäure; 3,5-Dibromthiosalicylsäure; 4-Methoxysulfonylthiosalicylsäure; 4-Methoxythiosalicylsäure; 4-Methoxy-2-mercaptobenzoesäure; 4-Chlor-2-mercaptobenzoesäure; 4-Methoxy-2-nitroanilin; Diazotierung von 4-Methoxy-2-nitroanilin; 4-Amino-3-nitroanisol; 4-Methoxy-2-nitrobenzonitril; Hydrolyse zu 4-Methoxy-2-nitrobenzoesäure; Reduktion von 4-Methoxy-2-nitrobenzoesäure zu 4-Methoxyanthranilsäure mit Eisenpulver in Salzsäure; 4-Methoxy-2-aminobenzoesäure; 4-Methoxy-2-mercaptobenzoesäure; 4-Methoxythiosalicylsäure
Copare also: Katz, L.: US Patent Appl. US 2767173.

Author(s): A. Hantzsch and G. Osswald
Title: Über die Umwandlung von Farbbasen in Pseudoammonium-Hydrate, -Cyanide and -Sulfonsäuren
Ber. dtsch. Chem. Ges. Vol. 33, p. 278-317 (1900); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): F. Ullmann and P. Dootson
Title: Untersuchungen über Farbstoffe der Anthrachinon-Acridon-Reihe
Ber. dtsch. Chem. Ges. Vol. 51, p. 9-24 (1918); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Nitrierung von 4-Aminotoluol; 2-Nitrotoluidin; 4-Amino-2-nitrotoluol; 4-Hydroxy-2-nitrotoluol; 2-Nitro-p-kresol; 4-Methoxy-2-nitrotoluol; 4-Methoxy-2-nitrobenzoesäure; 2-Nitro-4-methoxybenzoesäure; 4-Methoxy-2-aminobenzoesäure; 2-Amino-4-methoxybenzoesäure; 4-Methoxyanthranilsäure; 2- Amino-4-methoxybenzoesäure; 2-Nitro-4-methoxybenzoesäure

Author(s): P. Friedländer
Title: Zur Kenntnis des Farbstoffes des antiken Purpurs aus Murex brandaris
Monatsh. Chem. Vol. 30, p. 247-253 (1909); ISSN: 0026-9247; CODEN: MOCMB7

keywords: 6,6'-Dibromindigo als Farbstoff des antiken Purpurs; Murex brandaris

Author(s): P. Friedländer, S. Bruckner and G. Deutsch
Title: Über Brom- and Methoxyderivate des Indigos
Justus Liebigs Ann. Chem. Vol. 388, p. 23-49 (1912); ISSN: 0075-4617; CODEN: JLACBF

keywords: 6,6'-Dibromindigo als Farbstoff des antiken Purpurs; Murex brandaris; 4,4'-Dibromindigo; 5,5'-Dibromindigo; 7,7'-Dibromindigo; 2-Nitro-6-bromtoluol; 6-Brom-2-toluidin; Acetamido-p-kresol; Nitro-p-kresol; 3-Nitro-4-methylphenol; 3-Acetamido-4-methylphenol; 2-Acetamido-4-methoxytoluol; 4-Methoxyacetanthranilsäure; 4-Methoxyanthranisäure; 4-Methoxy-2-aminobenzoesäure; 2-Amino-4-methoxybenzoesäure; 3-Acetamido-4-methylanisol

Author(s): M. Watanabe, M. Date, M. Tsukazaki and S. Furukawa
Title: Regioselective syntheses of substituted thioxanthen- and selenoxanthen-9-one derivatives
Chem. Pharm. Bull. Vol. 37, No. 1, p. 36-41 (1989); ISSN: 0009-2363; CODEN: CPBTAL

keywords: substituierte Thioxanthone and Selenoxanthone; 3-Methoxythiosalicylsäureamid; 4-Methoxythiosalicylsäureamid; 3-Methoxy-2-mercaptobenzoesäureamid; 4-Methoxy-2-mercaptobenzamid

Inventor(s): Rudolf Lesser
Title: Verfahren zur Darstellung von Arylthioglykol-o-carbonsäuren and deren Estern
(Dr. Rudolf Lesser, Berlin) Dtsch. Reichspat. DE 229067, (29.11.1910); Patent Class.: 07C149/40

Author(s): A. Barker and C.C. Barker
Title: 3,6-disubstituted Fluorenes. Part I. The attempted introduction of a 6,6'-Methylene bridge directly into 3,3'-Diaminodiphenyl and some of its derivatives
J. Chem. Soc., p. 2034-2036 (1953); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): A. Barker and C.C. Barker
Title: 3,6-disubstituted Fluorenes. Part II. The preparation of 3,6-diaminofluorene from fluorene, and the attemted internuclear cyclisation of derivatives of 4,4'-Diaminodiphenylmethane
J. Chem. Soc., p. 870-873 (1954); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): A. Barker and C.C. Barker
Title: 3,6-disubstituted Fluorenes. Part III. Fluorene analogues of Michler's Hydrol, Malachite-green, and Cystal-violet.
J. Chem. Soc., p. 1307-1309 (1954); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): J. Wislicenus
Title: Ueber die Produkte der Einwirkung von Phthalyldichlorür auf Natriummalonsäureester
Justus Liebigs Ann. Chem. Vol. 242, p. 23-93 (1887); ISSN: 0075-4617; CODEN: JLACBF

Author(s): L.N. Goldyrev and G.P. Nuzhdina
Title: Isomerization of Acetylenediphthalide
Sbornik Statei Obshchei Khim. Vol. 2, p. 1275-1277 (1953); CODEN: 19HMAJ

keywords: 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): J. Suszko and L. Wójcinski
Title: Über einige Umwandlungen des Phthalyl-malonsäureesters
Ber. dtsch. Chem. Ges. Vol. 69, p. 2452-2455 (1936); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 1,3-Indandion; Bindon; Phthalylessigsäure; Truxenchinon; Isomerisieerung von Phthalylessigsäure in saurem Medium; Einwirkung von Schwefelsäure auf Phthalylmalonsäureester

Author(s): T. Posner and R. Hofmeister
Title: Beiträge zur Kenntnis der Indigo-Gruppe, VII. Vorläufige Mitteilungen über die Konstitution des Küppenfarbstoffes Indiogelb 3 G Ciba
Ber. dtsch. Chem. Ges. Vol. 59, p. 1827-1835 (1926); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Umlagerung von "Indenigo" zu 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Wasseranlagerung an Diphthalylethen; Mechanismus

Author(s): G. Wanag
Title: Bis-[indandion-carbonsäure-äthylester]
Ber. dtsch. Chem. Ges. Vol. 72, p. 973-976 (1939); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Umlagerung von 2,2-Bis(1,3-indandion-2-carbonsäureethylester) zu 6,11-Dihydroxynaphthacenchinon unter dem Einfluß von Säure; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Wasseranlagerung an Diphthalylethen; Mechanismus; Dimerisierung von Natrium-1,3-Indandion-2-carbonsäureethylester mit Blei(IV)-oxyd

Author(s): V. Kaufmann
Title: Ueber ein Analogon des Indigos in der Indenreihe: Diphthalyläthen
Ber. dtsch. Chem. Ges. Vol. 30, p. 382-387 (1897); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 2,2-Dibrom-1,3-indandion; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): S. Gabriel and E. Leupold
Title: Umwandlungen des Aethindiphtalids. I.
Ber. dtsch. Chem. Ges. Vol. 31, p. 1159-1174 (1898); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 2,2-Dibrom-1,3-indandion; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): S. Gabriel and E. Leupold
Title: Umwandlungen des Aethindiphtalids. II.
Ber. dtsch. Chem. Ges. Vol. 31, p. 1272-1286 (1898); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 2,2-Dibrom-1,3-indandion; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): F. Nathanson
Title: Umlagerungen von Phtalidderivaten in Abkömmlinge des a,g-Diketohydrindens
Ber. dtsch. Chem. Ges. Vol. 26, p. 2576-2582 (1893); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Phthalylessigsäure; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): A. Michael and S. Gabriel
Title: Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride
Ber. dtsch. Chem. Ges. Vol. 10, p. 391-393 (1877); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): A. Michael and S. Gabriel
Title: Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride. II. Mittheilung
Ber. dtsch. Chem. Ges. Vol. 10, p. 1551-1562 (1877); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): A. Michael and S. Gabriel
Title: Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride. III. Mittheilung
Ber. dtsch. Chem. Ges. Vol. 10, p. 2199-2210 (1877); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): A. Michael and S. Gabriel
Title: Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride. IV. Mittheilung
Ber. dtsch. Chem. Ges. Vol. 11, p. 1007-1021 (1878); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): A. Michael and S. Gabriel
Title: Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride. V. Mittheilung
Ber. dtsch. Chem. Ges. Vol. 11, p. 1679-1683 (1878); ISSN: 0365-9496; CODEN: BDCGAS

Author(s): A. Schönberg and R.C. Azzam
Title: Reactive methylene groups and nitroso-compounds. Abnormal action of acids on 1,2,3-Triketones
J. Chem. Soc., p. 1428-1430 (1939); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Bis-indandion aus Ninhydrin

Author(s): A. Schönberg and R. Moubasher
Title: Studies on Indene Derivatives. Part III. The constitution and some reactions of Bishydroxyindone. The photochemical reduction of Triketohydrindene
J. Chem. Soc., p. 366-367 (1944); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Bis-indandion aus Ninhydrin

Author(s): A. Schönberg and R. Moubasher
Title: Studies on Indene Derivatives. Part IV. Synthesis of Bis-1,3-diketoindanylidene and experiments with "Ninhydrin" (Triketoindane hydrate)
J. Chem. Soc., p. 212-214 (1949); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Bis-indandion aus Ninhydrin; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): A. Schönberg, N. Latif, R. Moubasher and W.I. Award
Title: Photochemical Reactions. Part XV. (a) Photopolymerisation of Coumarins and related substances. (b) Photo-addition and reduction process of aromatic ketones
J. Chem. Soc., p. 374-379 (1950); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Bis-indandion aus Ninhydrin; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): A. Schönberg and E. Singer
Title: Über nicht katalysierte Aldol-additionen an hydratbildenden Ketocarbonylverbindungen
Chem. Ber. Vol. 103, p. 3871-3884 (1970); ISSN: 0009-2940; CODEN: CHBEAM

keywords: Addition von 1,3-Indandion an Ninhydrin; Bis-indandion

Author(s): G.A. Russell and M.C. Young
Title: Semidiones. III. Radical ions derived from Ninhydrin and Alloxan
J. Am. Chem. Soc. Vol. 88, p. 2007-2014 (1966); ISSN: 0002-7863; CODEN: JACSAT

keywords: Bis-indandion aus Ninhydrin; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): G.A. Russell and F.A. Neugebauer
Title: Electron transfer processes - X: radical ions with hydrogen bridges derived from 1,1',3,3'-tetraketo-D2,2'-bindan, 5,6,11,12-naphthacenetetrone, 1,4,9,10-anthracenetetrone, and 1,4,5,8-naphthalenetetrone
Org. Magn. Res. Vol. 1, p. 125-137 (1969); ISSN: 0030-4921; CODEN: ORMRBD

keywords: Bis-indandion aus Ninhydrin; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): F. Campagna, A. Carotti, G. Casini and M. Ferappi
Title: Reaction of Trifluoroacetic anhydride on adducts derived from 1,2,3-Indanetrione with cyclic CH-acid compunds
Gazz. Chim. Ital. Vol. 113, p. 507-513 (1983); ISSN: 0016-5603; CODEN: GCITA9

keywords: Ninhydrin; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): F. Campagna, A. Carotti, G. Casini and M. Ferappi
Title: Reaction of aldol adducts from 1,2,3-indanetrione and cyclic CH-acid compounds: keto-enol tautomeric study of the reduction products
Gazz. Chim. Ital. Vol. 115, p. 515-522 (1985); ISSN: 0016-5603; CODEN: GCITA9

keywords: Ninhydrin; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): W. Wislicenus
Title: Zur Geschichte des Anhydo-bisdiketohydindens (Bindons)
Ber. dtsch. Chem. Ges. Vol. 31, p. 2935-2938 (1898); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Bindon; 1,3-Indandion

Author(s): H. Voswinckel
Title: Über Bisdiketohydrinden
Ber. dtsch. Chem. Ges. Vol. 42, p. 465-470 (1909); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): E. Hoyer
Title: Über einige Abkömmlinge des Anhydro-bisdiketohydrindens
Ber. dtsch. Chem. Ges. Vol. 34, p. 3269-3274 (1901); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Bindon; Dibrombindon

Author(s): G. Wanag
Title: Direkte Umwandlung des Bis-Indandions in Dioxynaphthacenchinon
Ber. dtsch. Chem. Ges. Vol. 70, p. 274-277 (1937); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Bis-indandion; 6,11-Dihydroxynaphthacenchinon; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): A. Hantzsch and J. Lister
Title: Über Bis-Indandion- and Bis-Oxindon-Derivate
Justus Liebigs Ann. Chem. Vol. 392, p. 319-322 (1912); ISSN: 0075-4617; CODEN: JLACBF

keywords: Bis-indandion; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): G. Wanag
Title: Oxidationsprodukte von Indandion-1,3 and von Bindon
Justus Liebigs Ann. Chem. Vol. 494, p. 107-116 (1932); ISSN: 0075-4617; CODEN: JLACBF

keywords: Bindon; Bis-bindon; Bis-indandion; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): G. Wanag
Title: Zur Kenntnis der Bis-bindonylene: cis-Bis-Bindonylen
Justus Liebigs Ann. Chem. Vol. 510, p. 280-287 (1934); ISSN: 0075-4617; CODEN: JLACBF

keywords: Bindon; Bis-bindon; Bis-indandion; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): J.C. Eck and C.S. Marvel
Title: The synthesis of Bis-2,2'-(1,3-diphenylindenol-3). A contribution to the Rubrene problem
J. Am. Chem. Soc. Vol. 57, p. 1898-1900 (1935); ISSN: 0002-7863; CODEN: JACSAT

keywords: Addition von Phenylmagnesiumbromid an Bis-indandion; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): D.F. Lynch and J.D. Reid
Title: The Ketonimine dyestuffs and their derivatives
J. Am. Chem. Soc. Vol. 55, p. 2515-2520 (1933); ISSN: 0002-7863; CODEN: JACSAT

keywords: Auramin; 4,4'-Bis(dimethylamino)benzophenonimin; Michler's Keton; Chlorierung mit Phosphorpentachlorid; Phosphorylchlorid; Phosphoroxychlorid

Author(s): J.F. Honek, M.L. Mancini and B. Belleau
Title: o-Chlororsulfenylbenzoyl chloride: a useful reagent in the synthesis of Thioxanthones
Synth. Commun. Vol. 13, No. 12, p. 977-983 (1983); ISSN: 0039-7911; CODEN: SYNCAV

keywords: 9-Thioxanthone durch Friedel-Crafts-Acylierung mit o-Chlorsulfenylbenzoesäurechlorid; Spaltung einer Disulfid-Gruppierung mit Chlor

Author(s): E. Noelting and H. Blum
Title: Ueber Derivate des Diketohydrindens (Indandions)
Ber. dtsch. Chem. Ges. Vol. 34, p. 2467-2471 (1901); ISSN: 0365-9496; CODEN: BDCGAS

keywords: Kondensation von 1,3-Indandion mit aromatischen Aldehyden; o-Aminobenzaldehyd; 2-Aminobenzaldehyd; p-Dimethylaminobenzaldehyd; 2-(4-Dimethylaminobenzyliden)-1,3-indandion

Author(s): M. Polonovski and D. Libermann
Title: Sur les thiouraciles condensés
Bull. Soc. Chim. Fr., p. 1073-1075 (1947); ISSN: 0037-8968; CODEN: BSCFAS

keywords: 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): M.C. Dufraisse
Title: Sur la constition naphtacénique des rubènes. I.
Bull. Soc. Chim. Fr., Ser. 5 Vol. 3, p. 1847-1857 (1936); ISSN: 0037-8968; CODEN: BSCFAS

keywords: 2,2'-Bis-diketohydrindene; Bis-indandion; 2,2'-Bis(dioxyhydrindene); 2,2'-Bis(1,3-indandion); 2-(1,3-Indandion-2-yliden)-1,3-indandion; 2,2'-Bis-(1,1',3,3'-tetraoxoindan); Diphthalylethen; Indenigo

Author(s): K. Matsumura
Title: The synthesis of certain acridine compounds
J. Am. Chem. Soc. Vol. 51, p. 816-820 (1929); ISSN: 0002-7863; CODEN: JACSAT

keywords: Umwandlung von 3,6-Diaminoacridon in 3,6-Dihydroxyacridon (keine Diazotierung, aber Hydrolyse mit konz. Schwefelsäure bei 190 °C); 3,6-Dimethoxyacridon; 3,6-Dimethoxy-10-methylacridon; 9-Chlor-3,6-dimethoxy-10-methylacridinium-chlorid; 2,2',4,4'-Tetranitrodiphenylmethan; 2,2',4,4'-Tetranitrobenzophenon; 3,6-Diaminoacridon; 3,6-Dihydroxyacridon; 3,6-Dihydroxyacrid-9-on; 3,6-Diaminoacrid-9-on; 9-Chlor-3,6-Diaminoacridin; 3,6-Dimethoxyacridon; 3,6-Dimethoxyacrid-9-on; 9-Amino-3,6-dihydroxyacridin; 9-Acetamido-3,5-dimethoxyacridin; 9-Acetamido-3,5-dimethoxyacridin-10-methylacridinium-p-toluolsulfonat; 9-Acetamido-3,5-dimethoxyacridin-N-methylacridinium-p-toluolsulfonat; 9-Amino-3,5-dimethoxyacridin-10-methylacridinium-chlorid; 9-Amino-3,5-dimethoxyacridin-N-methylacridinium-chlorid
Vergleiche Hata, S.; Matsumura, K.; Ishihara, K.: US Pat. Appl. US 2083908.

Author(s): R.H. Nealey and J.S. Driscoll
Title: Synthesis of 3,6-bis(dimethylamino)thio- and selenoxanthene
J. Heterocyclic Chem. Vol. 3, p. 228-229 (1966); ISSN: 0022-152X; CODEN: JHTCAD

keywords: thiopyronine; 3,6-bis(dimethylamino)-thioxanthone; BTX; 3,6-bis(dimethylamino)-selenoxanthone; 3,6-bis(dimethylamino)-thioxanth-9-one; 3,6-bis(dimethylamino)-selenoxanth-9-one; 3,6-bis(dimethylamino)-thioxanthen; 3,6-bis(dimethylamino)-selenoxanthen; 3,6-bis(dimethylamino)-thioxanthylium-chloride - zinc chloride double salt; 3,6-bis(dimethylamino)-selenoxanthylium-chloride - zinc chloride double salt

Author(s): M. Battegay and G. Hugel
Title: 3,6-Tetramethyldiaminocyanoselenopyronine
Bull. Soc. Chim. Fr. Vol. 31, p. 440-444 (1922); ISSN: 0037-8968; CODEN: BSCFAS

keywords: selenopyronine; 3,6-bis(dimethylamino)-selenoxanthone; 3,6-bis(dimethylamino)-selenoxanth-9-one; 3,6-bis(dimethylamino)-selenoxanthene; 3,6-bis(dimethylamino)-selenoxanthylium-chloride-zinc chloride-double salt

Author(s): M. Morita and S. Kato
Title: Flash photolysis of thiopyronine
Z. Naturforsch. Vol. 23B, p. 931-933 (1968); ISSN: 0044-3174; CODEN: ZENBAX

keywords: absorption maximum; BTX; 3,6-bis(dimethylamino)thioxanthene; 3,6-bis(dimethylamino)thioxanth-9-one; thiopyronine
Abstract:
Flash photolytic investigation of photosensitizing dye "thiopyronine" was undertaken with and without redox substrates. Flash excitation of thiopyronine deaerated buffered solution without any substrate produced three transient intermediates ; triplet state (D^t) ; half-oxidized form (Oxd) and half-reduced form or semiquinone (Red) of the dye. Red and Oxd were generated through the electron transfer reactions, D^t-D^t and D^t-D (D is a dye molecule in the ground state). Absorption spectra of these intermediates were identified and their reaction mechanisms were
established. The high efficiency of this dye in the photodynamic effect was discussed in connection with the high quantum yield of triplet state production and photochemical redox reversibility of the dye.

Author(s): M. Morita and S. Kato
Title: Studies of the transient intermediates of a thiopyronine aqueous solution under flash excitation
Bull. Chem. Soc. Jpn. Vol. 42, p. 25-35 (1969); ISSN: 0009-2673; CODEN: BCSJA8

keywords: absorption maximum; BTX; 3,6-bis(dimethylamino)thioxanthene; 3,6-bis(dimethylamino)thioxanth-9-one; thiopyronine
Abstract:
Flash photolytic studies of the transient intermediates produced in the flash excitation of an aqueous buffered solution of the photosensitizing dye "thiopyronine" were undertaken in order to obtain direct insight into the reaction mechanism of the photosensitizing action of the dye. As had been expected from the structural similarity to a well-known photosensitizer, methylene blue, previously reported on the flash excitation of thiopyronine, in a deaerated buffered solution at pH 7.4 without any substrate, produced three transient intermediates: a triplet-state (D^t), a half-oxidized form (Oxd), and a half-reduced form or semiquinone (Red) of the dye. Red and Oxd were generated simultaneously through electron transfer reactions, i. e., D^t+ D^t ---> Red+ Oxd and D^t + D ---> Red + Oxd, where D is the dye in the ground state. Thiopyronine solutions containing some reducing and oxidizing agents were studied in order to identify the intermediates. The absorption spectra of these intermediates were identified, and their reaction mechanism studied. The rate constants of some elementary processes were obtained. The high efficiency of thiopyronine in its photodynamic effect was discussed in connection with the high quantum yield of triplet-state production and the high reversibility of the photochemical redox reaction of the dye.

Author(s): G. Winter and U. Steiner
Title: Heavy atom substituents as molecular probes for sovent effects on the dynamics of short-lived triplet exiplexes
Ber. Bunsenges. Phys. Chem. Vol. 84, p. 1203-1214 (1980); ISSN: 0005-9021; CODEN: BBPCAX

keywords: absorption maximum; 3,6-bis(dimethylamino)thioxanthene; 3,6-bis(dimethylamino)thioxanth-9-one; thiopyronine; solvent effects; photochemistry; heavy atom effects; triplett exciplex
Abstract:
The influence of heavy atom substituents (Br, I) in the electron donor aniline on the electron transfer reaction with thiopyronine triplet is investigated by flash spectroscopy in solvents of different viscosity and polarity. Triplet quenching constants and radical yields are determined. The results are analysed in terms of decay constants of an intermediate triplet exciplex where the heavy atom substituents significantly enhance the intersystem crossing process leading to singlet ground state formation and thus diminishing the radical yield due to exciplex dissociation. The sensitivity of the radical yield to solvent effects is strongly enhanced by heavy atom substitution though the solvent effects proper on the exciplex dynamics are substituent independent. The heavy atom effect is used to study the solvent cage effect on exciplex dissociation by means of viscosity variation. The exciplex dissociation lifetime is proportional to solvent viscosity, however, it contains a constant contribution which may be attributed to exciplex bonding. By means of the heavy atom probes it is found that in-creasing solvent polarity intersystem crossing in the exciplex is favored over exciplex dissociation into radicals. A tentative explanation is given in terms of solvent polarity dependence of the electronic energy gap between exciplex and corresponding Franck-Condon ground state.

Author(s): K. Kikuchi, M. Ozaki and H. Kokubun
Title: Determination of the S*-T transition probabilities of some acridine dyes and of thiopyronine by the method of sensitized delayed fluorescence
J. Photochem. Vol. 16, p. 19-29 (1981); ISSN: 0047-2670 / 0300-9424; CODEN: JPCMAE

keywords: absorption maximum; eosin; erythrosin; acridine orange; acriflavine; 3,6-bis(dimethylamino)thioxanthene; 3,6-bis(dimethylamino)thioxanth-9-one; thiopyronine; thiopyronin
Abstract:
Parker's method of delayed fluorescence as a means of determining the S*-T transition probability F_ST was extended to systems in which reversible triplet energy transfer occurs between donor and acceptor. The F_ST values of proflavine, acriflavine and acridine orange in ethanol were determined by this extended method using anthracene or 9-methylanthracene as an acceptor and eosine as a reference donor. The F_ST values thus obtained are 0.45 ± 0.05 (proflavine), 0.53 ± 0.07 (acriflavine) and 0.30 ± 0.05 (acridine orange). The F_ST values of eosine and thiopyronine were also determined by the method in Parker's original form using perylene as an acceptor and erythrosine as a reference donor. The F_ST values obtained, 0.44 ± 0.01 (eosine) and 0.24 (thiopyronine), agree satisfactorily with those obtained by a chemical method, 0.43 ± 0.04 (eosine) and 0.28 ± 0.03 (thiopyronine).

Author(s): C.D. Ritchie, C. Kubisty and G.Y. Ting
Title: Cation-Anion combination reactions. 22. Rate and equilibrium constants for reactions of pyronine and thiopyronine with nucleophiles
J. Am. Chem. Soc. Vol. 105, p. 279-284 (1983); ISSN: 0002-7863; CODEN: JACSAT

keywords: absorption maximum; 3,6-Bis(dimethylamino)thioxanthene; 3,6-Bis(dimethylamino)thioxanth-9-one; Thiopyronine; Pyronine Y; Tetrafluoroborate-salt

Author(s): Y. Tanaka, H. Akisada, T. Fujimoro and N. Nishino
Title: Fluorescence energy transfer to tailed acridine oranges from pyrene excimer formed in four a-helix bundle 53-peptide
Chem. Lett., p. 135-136 (1996);

keywords: 3,6-Bis(dimethylamino)acridine; 10-Methyl-3,6-Bis(dimethylamino)acridinium bromide; N-Methyl-3,6-Bis(dimethylamino)acridinium-iodide; Acridin Orange
Abstract:
Fluorescence energy transfer from pyrene excimer in four a-helix bundle polypeptide to 10-n alkyl acridine oranges was alkyl chain-length-dependent. The hydrophobic space in the bundle structure could accommodate as long alkyl chain as decyl by 1:1 stoichiometry.

Author(s): A. Schönberg and R. Moubasher
Title: Studies on Indene Derivatives. Part II. Triketohydrindene
J. Chem. Soc., p. 71-72 (1943); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Dehydration of Ninhydrine with Thionyl chloride

Author(s): A. Schönberg and A. Mustafa
Title: Photochemical Reactions. Part VII. Reactions in sunlight involving (a) rupture of the ethane linkage, (b) Dehydrogenation effected by quinone and benzophenone derivatives, (c) addition reactions between ketones and methanes
J. Chem. Soc., p. 67-71 (1944); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): A. Schönberg, A.F. Aly Ismail and W. Asker
Title: Reactions of thermochromic ethylenes
J. Chem. Soc., p. 442-446 (1946); ISSN: 0368-1769; CODEN: JCSOA9

keywords: N,N'-Dimethyl-9,9'-diacridylidene

Author(s): A.F. Aly Ismail and Z.M. El-Shafei
Title: Photodehydrogenation and photo-oxidation of some thermochromic ethylenes and related compounds
J. Chem. Soc., p. 3393-3396 (1957); ISSN: 0368-1769; CODEN: JCSOA9

keywords: thermochromic ethylenes; olefines

Author(s): A. Schönberg, A. Mustafa and M.E. El-Din Sobhy
Title: Thermochromism of Dixanthylenes
J. Am. Chem. Soc. Vol. 75, p. 3377-3378 (1953); ISSN: 0002-7863; CODEN: JACSAT

keywords: Thermochromic Ethylenes; Olefines; 2-(9-Xanthylidene)-1,3-indandione; 2-(9-Thioxanthylidene)-1,3-indandione

Author(s): A. Schönberg, E. Singer and W. Stephan
Title: Extremely reactive carbon-carbon double bonds. I. Reactions with 2-(9-Xanthylidene)-, 2-(9-Thioxanthylidene)-, and 2-(9-Fluorenylidene)-1,3-indandione. A contribution on the structure and reactivity of non-planar C-C double bonds
Tetrahedron Vol. 39, No. 14, p. 2429-2437 (1983); ISSN: 0040-4020;

keywords: thermochromic ethylenes; olefines; 2-(9-xanthylidene)-1,3-indandione; 2-(9-thioxanthylidene)-1,3-indandione; 2-(9-fluorenylidene)-1,3-indandione

Author(s): B. Chauncy und E. Gellert
Title: A new variation of the Pschorr synthesis
Aust. J. Chem. Vol. 22, p. 993-995 (1969); ISSN: 0004-9425; CODEN: AJCHAS

keywords: Diazotierung mit Isopentylnitrit (Amylnitrit) in 20 % wässeriger Schwefelsäure; 2-Iodzimtsäureester; 9-Phenanthrencarbonsäuren

Author(s): G.A. Bihlmayer, F.J. Kunz und O.E. Polansky
Title: Umsetzungen einiger Ketimine mit Meldrum's Säure, Dimedon, Indandion-1,3 und Perinaphthindandion-(1,3)
Monatsh. Chem. Vol. 97, p. 1293-1298 (1966); ISSN: 0026-9247; CODEN: MOCMB7

keywords: Thermochrome Ethylene; Olefine; 2-(9-Fluorenylidene)-1,3-indandione; Kondensation von 1,3-Indandion mit Ketiminen; 2-(Diphenylmethylidene)-1,3-indandione

Author(s): E. Harnik, F.H. Herbstein, G.M.J. Schmidt und F.L. Hirshfeld
Title: The structure of overcrowded aromatic compounds. Part I. A preliminary survey
J. Chem. Soc., p. 3288-3294 (1954); ISSN: 0368-1769; CODEN: JCSOA9

keywords: N,N'-dimethyl-9,9'-diacridylidene; 9,9-difluorenylidene; dixanthylidene (Dianthrone); dianthronylidene

Author(s): E. Harnik und G.M.J. Schmidt
Title: The structure of overcrowded aromatic compounds. Part II. The crystal structure of Dianthronylidene
J. Chem. Soc., p. 3295-3302 (1954); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Dixanthylidene (Dianthrone), Dianthronylidene

Author(s): F.H. Herbstein und G.M.J. Schmidt
Title: The structure of overcrowded aromatic compounds. Part III. The crystal structure of 3,4-Benzophenanthrene
J. Chem. Soc., p. 3302-3313 (1954); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): J.J. Stezowski, P.U. Biedermann, T. Hildenbrand, J.A. Dorsch, C.J. Eckhardt und I. Agranat
Title: Overcrowded enes of the tricycloindane-1,3-dione series: interplay of twisting, folding and pyramidalization
J. Chem. Soc., Chem. Commun., No. 3, p. 213-215 (1993); ISSN: 0022-4936; CODEN: JCCCAT

keywords: Thermochromic Ethylenes; Olefines; 2-(9-Xanthylidene)-1,3-indandione; 2-(9-Thioxanthylidene)-1,3-indandione; Dixanthylenylidene; Bifluorenylidene

Author(s): J. Walker
Title: Chemotherapeutic agents of the sulfone type. Part I. Sulphones containing a p-Aminophenyl group
J. Chem. Soc., p. 630-633 (1945); ISSN: 0368-1769; CODEN: JCSOA9

Author(s): A.T. Fuller, I.M. Tonkin und J. Walker
Title: Chemotherapeutic agents of the sulfone type. Part II. Sulphones related to benzamide and Benzylamine
J. Chem. Soc., p. 633-640 (1945); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Diazotierung von aromatischen Aminen unter Einführung der Nitril-Gruppe; Benzonitrile; Umsetzung des Diazonium-salzes mit Natriumcyanid-Nickelchlorid, verbesserte Ausbeute gegenüber der Verwendung von Kupfercyanid

Author(s): J.M.L. Stephen, I.M. Tonkin und J. Walker
Title: Tetrahydroacridones and related compounds as antimalarias
J. Chem. Soc., p. 1034-1039 (1947); ISSN: 0368-1769; CODEN: JCSOA9

keywords: Diazotierung von 2-Nitro-4-aminoanisol mit Einführung der Nitril-Gruppe; 2-Nitro-4-methoxyanilin; 2-Nitro-4-methoxybenzonitril; 2-Nitro-4-methoxyphenylcyanid; 2-Nitro-4-methoxybenzoesäure; 4-Methoxy-2-nitrobenzoesäure; 4-Methoxy-2-aminobenzoesäure; 2-Amino-4-methoxybenzoesäure; 4-Methoxyanthranilsäure; 2- Amino-4-methoxybenzoesäure; Umsetzung des Diazonium-salzes mit Natriumcyanid-Nickelchlorid, verbesserte Ausbeute gegenüber der Verwendung von Kupfercyanid

Author(s): A. Maassen
Title: Zur Kenntnis der Amidokresole
Ber. dtsch. Chem. Ges. Vol. 17, p. 608-610 (1884); ISSN: 0365-9496; CODEN: BDCGAS

keywords: 4-methyl-3-aminophenol; o-aminokresol; 2-amino-4-hydroxy-toluol; o-acetamidokresol

Author(s): M.T. Bogert und W.F. Hand
Title: The synthesis of alkylketodihydroquinazolines from anthranilic nitrile
J. Am. Chem. Soc. Vol. 24, p. 1031-1050 (1902); ISSN: 0002-7863; CODEN: JACSAT

keywords: o-nitrobenzonitrile; 2-nitrophenylcyanide; 2-aminobenzonitrile; anthranilnitrile; reduction of 2-nitrobenzonitrile mit SnCl₂ hydrochloric acid

Author(s): T. Scholl und H.J. Roth
Title: Umlagerung von 10,11-Epoxycarbamazepin zu schwefelhaltigen Acridin-Derivaten
Arch. Pharm. Vol. 318, p. 634-639 (1985);

keywords: N-Acetyl-acridan-9-carbaldehyd-dimethylacetal; N-Acetyl-acridan-9-carbaldehyd-dimethylketal; 10-Acetyl-9-acridanaldehyd-dimethylthioacetal