Investigations in the imidazole series LXXII. Synthesis of naphth[1,2-d]imidazo[3,2-b]-3-thiazolidone and its derivatives

Naphth1,2-d]imidazo3,2-b]-3-thiazolidone and its methyl homolog were synthesized by the reaction of 2-mercaptonaphth1,2-d]imidazole with chloroacetic and -chloropropionic acids with subsequent cyclization of the naphth1,2-d]imidazole-2-mercaptoacetic acids. The reactions of the first of them at the methylene group with aldehydes, nitroso compounds, and benzenediazonium salts were studied; the corresponding arylidene and azomethine derivatives of naphthimidazo-3-thiazolidone and the arylhydrazones of naphth1,2-d]imidazo3,2-b]thiazoline-2,3-dione were obtained. The arylidene derivatives of naphthimidazo-3-thiazolidone were also obtained by the reaction of naphthimidazole-2-mercaptoacetic acid or its methyl ester with aldehydes or (in one step) by the reaction of 2-mercaptonaphth1,2-d]imidazole with chloroacetic acid and carbonyl compounds.See 1] for communication LXXI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 399–402, March, 1972.