- Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones
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Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10- dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones.
- Kargina,Gornostaev,Nefedov
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- REACTION OF 6-OXO-6H-ANTHRAISOXAZOLES WITH CYCLOHEXENE
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The reaction of 6-oxo-6H-anthraisoxazoles with cyclohexene in the presence of aluminum chloride leads to the corresponding 1-cyclohexylamino-9,10-anthraquinones.
- Gornostaev, L. M.,Medvedeva, S. A.
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p. 1547 - 1549
(2007/10/02)
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- CHARACTERISTICS OF THE ALKOXYLATION OF HALOGENO-6-OXO-6H-ANTHRAISOXAZOLES
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The alkylation of 6-oxo-6H-anthraisoxazoles containing a chlorine or bromine atom at position 3 and also a bromine at position 5 takes place with substitution of the halogen or hydrogen, depending on the structure of the alkoxide ion and the type of halogen.
- Es'kin, A. P.,Gornostaev, L. M.,Zeibert, G. F.,Bogdanchikov, G. A.,El'tsov, A. V.
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p. 162 - 167
(2007/10/02)
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- REACTION OF 6H-6-OXOANTHRAISOXAZOLES WITH ALKYL PHENYL ETHERS AND DIMETHYLANILINE
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The reactions of halogen-substituted 6H-6-oxoanthraisoxazoles with alkyl phenyl ethers or dimethylaniline in the presence of aluminum chloride lead to the formation of 1-amino-2-chloro-4-(4-alkoxyphenyl)anthraquinones or 1-amino-2,4-di(4-dimethylaminophenyl)anthraquinone and simultaneous reduction of the heterocycle.
- Gornostaev, L. M.,Es'kin, A. P.,El'tsov, A. V.
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p. 200 - 202
(2007/10/02)
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- The Schmidt reaction of anthraquinones
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Schmidt reaction (sodium azide/sulfuric acid) of 1,5- and of 1,8-dichloroanthraquinones gives, in each case, both of the theoretically possible lactams (2,3,5,6-dibenzoazepin-4,7-diones).Two of the four theoretically possible lactams have been identified from Schmidt reaction of 1- and 2-chloroanthraquinones respectively.Methods used include:(a) preferential hydrolysis of one lactam and identification of the isomeric aminoanthraquinone formed on cyclodehydration of the resulting amino acid; (b) identification of the isomeric aminoanthraquinone(s) formed on direct treatment of a lactam (or mixture of lactams) by sulfuric acid; (c) cleavage by potassium tert-butoxide of the amino acid formed by preferential hydrolysis of one lactam and identification of the resulting benzoic acid as its methyl ester.
- Flemming, Cecily A.,Gandhi, Sham S.,Gibson, Martin S.,Ruediger, Edward H.
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p. 624 - 628
(2007/10/02)
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