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Paper | Regular issue | Vol 29, No. 8, 1989, pp.1583-1588
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5016
Ring Transformation of 5-Acylpyrimidines into 4-Acylpyrazoles with Phenylhydrazine

Abdelilah Bajnati, Michel Hubert-Habart,* Kaname Takagi, and Hiroshi Terada

*Section de Physique et Chimie, Institut Curie, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 05, France

Abstract

Phenylhydrazine in alcoholic acidic medium exclusively transformed 5-benzoyl-4-methyl-2-methylthiopyrimidine into 4-acetyl-1,3-diphenylpyrazole and 5-acetyl-2-methylthio-4-phenylpyrimidine into 4-benzoyl-3-methyl-1-phenylpyrazole. The mechanism of these ring contraction reactions is proposed.