Reaction of azomethines with acetoacetic ester

The reaction of (benzylidene) (2-naphthyl)amine with acetoacetic ester leads to ethyl 1-methyl-3-phenylbenzo [f]quinoline-2-carboxylate. Some reactions of this compound have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1082–1083, August, 1973.     

Reaction of o-diaminoanthraquinones with malonic ester

The reaction of 1,2- and 2,3-diaminoanthraquinones with malonic ester was studied. It was established that the reaction products are N-ethoxymalonyl-o-diaminoanthraquinones and their heterocyclic derivatives — 1H-2-ethoxycarbonylmethylanthraimidazolediones. N-Ethoxymalonlyl-2,3-anthraquinone undergoes cyclization to 1H-2,3,4,5-tetrahydroanthra(2,3-b]-1,4-diazepine-2,4,7,12-tetraone when it is heated with sodium methoxide in absolute methanol, whereas 2-N-ethoxymalonyl-1,2-diaminoanthraquinone undergoes cyclization to 1H-2-ethoxy carbonylmethy lanthra-1,2-d]imidazole-6,11-dione.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 965–968, July, 1978.     

Reaction of acetoacetic ester with o-aminothiophenols

Benzothiazole derivatives were obtained by condensation of o-aminothiophenol with acetoacetic ester in xylene. 4-Methyl-2-mercaptoacetoacetanilide was isolated in the case of 5-methyl-2-aminothiophenol, whereas ethyl 3-(5-methyl-2-aminophenylmercapto)crotonate was isolated without a solvent in the presence of hydrochloric acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1049–1052, August, 1978.     

Reaction of oxiranecarbonitrile with L-cysteine methyl ester

The title reaction yields (3R,5R) and (3R,5S) isomers of methyl 5-cyanotetrahydro-1,4-2H-thiazine-3-carboxylate, together with methyl 2-acetylthiazole-4-carboxylate as a minor by-product. The stereochemistry of the tetrahydrothiazine derivatives is discussed.     

Reaction of 4-iminothiazolidinone-2 with acetoacetic ester

The reaction of 4-iminothiazolidinone-2 with acetoacetic ester and its alkyl and aralkyl derivatives gives derivatives of thiazolo-[4,5-b]pyridine, which form salts with alkalis and are acylated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1547–1549, November, 1989.     

Reaction of methyl ester of n-methylimidoacetic acid with chloral

Russian Chemical Bulletin -     

Reaction of o-diaminoanthraquinones with acetoacetic ester and crotonic acid

The reaction of 1,2 (and 2,3)-diamino-9,10-anthraquinones with acetoacetic ester and crotonic acid gave dihydro- and tetrahydroanthraquinonediazepinones, the structures of which were established on the basis of spectral data and chemical transformations.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1107–1112, August, 1982.     

Reaction of 4-methyl-1,2-phenylenediamine with acetoacetic ester

Depending on the reaction conditions, 4-methyl-1,2-phenylenediamine reacts with acetoacetic ester to form 4,7(or 8)-dimethyl-2,3-dihydro-1H-1,5-benzodiazepinones or 5(or 6)-methyl-1-isopropenylbenzimidazolones. During acid catalysis under mild conditions, the more basic diamine group initially reacts with acetoacetic ester to form ethyl 3-(2-amino-4-toluidino)-crotonate, which subsequently can be converted to the corresponding benzodiazepinone and 2,5-dimethylbenzimidazole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1556–1560, November, 1971.     

Reaction of trifluororacemic acid methyl ester with 1,3-dienes

The reaction of trifluororacemic acid with 1,3-dienes affords Diels-Alder reaction products in a high yield and with a high degree of specificity. Catalysis by SnCl₄ changes the course of the reaction of the ester with isoprene, affording an ene reaction product.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 141–145. January, 1991.     

Reaction of chloroacetylenephosphonate with acetoacetic ester and its analogs

Russian Journal of General Chemistry -     

Reaction of 2-aryl-1,3-dioxolanes with nitroacetic ester

Conclusions 2-Phenyl-1,3-dioxolane, and its derivatives with donor substituents in the aromatic ring, react with the methyl ester of nitroacetic acid in Ac₂O medium and in the presence of acid catalysts to give the methyl esters of the corresponding -nitrocinnamic acids.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 439–440, February, 1982.