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Communication | Regular issue | Vol 41, No. 2, 1995, pp.209-214
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6923
Cycloaddition Reactions of 7-Substituted Acenaphtho[1,2-d]pyrazolo[1,2-a]benzotriazoles with Dimethyl Acetylenedicarboxylate

Otohiko Tsuge*, Taizo Hatta, Masafumi Sugaya, Eiji Yunoki, Hidenori Gau, and Akikazu Kakehi

*Department of Industrial Chemistry, Kumamoto Institute of Technology, 4-22-1, Ikeda, Kumamoto 860, Japan


The reactions of the title 7-phenyl- and 7-methylacenaphthopyrazolobenzotriazoles (triazapentalenes) with dimethyl acetylenedicarboxylate gave a mixture of the corresponding initial azomethine imidic cycloadduct and its isomeric pyrazinopyrimidine, whose yields greatly depended on the reaction conditions. Structures of both the initial and isomeric products were determined by X-ray crystallographic analyses. The initial cycloadduct readily isomerized to the pyrazinopyrimidine. It has been found that the methyl-substituted pyrazinopyrimidine underwent the Michael-type addition reaction.