L. M. Gornostaev

Synthesis of 2-aryl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones by reaction of 2-benzylamino-1,4-naphthoquinones with nitric acid

Abstract2-Aryl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones were synthesized by treatment of 2-benzylamino-1,4-naphthoquinones with a mixture of nitric and sulfuric acids in acetic acid.

The Synthesis of Benzo[а]Phenazine-5,6-Dione 7-Oxides

Tetracyclic nitrogen-containing quinone derivatives exhibit various types of biological activity and show promise for practical applications [1, 2]. Linear and angular quinoid derivatives of benzophenazines are of particular interest. Thus, it was recently discovered that benzo[а]phenazine-5,6-dione derivatives, diimines in particular, may function as ligands for rhodium and ruthenium, and also possess selective anticancer activity [3]. We found that the 4-arylamino-1,2-naphthoquinones 1а-d were converted to the benzo[а]phenazine5,6-dione N-oxides 2а-d by treatment with nitrosylsulfuric acid that was prepared in situ from sodium nitrite and sulfuric acid [4], and using acetic acid as the solvent.

Synthesis of 3-alkyl-5-arylamino-6,11-dihydro-3H-anthra[1,2-d]-[1,2,3]triazole-6,11-dione 2-oxides by nitrosation of 3-alkylamino-5-arylamino-6H-anthra[1,9-cd]isoxazol-6-ones

Nitrosation of 3-alkylamino-5-arylamino-6H-anthra[1,9-cd]isoxazol-6-ones with sodium nitrite in acetic acid leads to the formation of the corresponding unstable N-nitroso derivatives which are converted into 3-alkyl-5-arylamino-6,11-dihydro-3H-anthra[1,2-d][1,2,3]triazole-6,11-dione 2-oxides on heating.

Cyclization of 2-arylamino-1,4-naphthoquinones to benzo[b]phenazine-6,11-dione 5-oxides

A method for the synthesis of a new group of tetracyclic diazaquinones, viz., benzo[b]-phenazine-6,11-dione 5-oxides, was developed and the pathways of their further modifications were outlined.

Synthesis of 6H-naphtho[1,2,3-cd]indol-6-ones

S,S-Dimethyl-and S-methyl-S-phenyl-N-(9,10-anthraquinon-1-yl)sulfoximides are converted into 6H-naphtho[1,2,3-cd]indol-6-ones on heating in polar aprotic solvents.

Synthesis of 13-alkylbenzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones by reaction of 2-alkylamino-1,4-naphthoquinones with ninhydrin

Reactions of 2-alkylamino-1,4-naphthoquinones with 2,2-dihydroxy-1H-indene-1,3(2H)-dione afforded 13-alkylbenzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones.

Synthesis of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones

The reaction of 2-amino(alkylamino)-1,4-naphthoquinones with nitrating mixture in concentrated sulfuric acid leads to the formation of 2-amino(alkylamino)-3-nitro-1,4-naphthoquinones.

Synthesis of 1-Aryl-5-Nitrobenzotriazoles*

3-Aryl-1-(3-nitrophenyl)triazenes were obtained in the cyclization reaction of diazotized 3-nitroaniline with arylamines in the presence of dimethyl sulfoxide and potassium carbonate to give 1-aryl-5-nitrobenzotriazoles.

Cyclization of 2-Azido-3-(alkyl-N-nitrosoamino)-1,4-naphthoquinones to 1-Alkyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 2-Oxides

Thermolysis of 2-azido-3-(alkyl-N-nitrosoamino)-1,4-naphthoquinones gives rise to compounds belonging to a new quinoid fused heterocyclic system, 1-alkyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione 2-oxides.

Transformation of 2-alkylamino-1,4-naphthoquinones into 2-alkylnaphtho[2,1-d][1,3]oxazole-4,5-dione 4-oximes by the action of nitrosylsulfuric acid

Abstract2-Alkylnaphtho[2,1-d][1,3]oxazole-4,5-dione 4-oximes were synthesized by reaction of 2-alkylamino-1,4-naphthoquinones with nitrosylsulfuric acid in acetic acid.