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Communication | Regular issue | Vol 63, No. 6, 2004, pp.1273-1279
Published online, 16th April, 2004
DOI: 10.3987/COM-04-10061
A Novel Ring-opening Reaction of (Z)-2-Methyl-4-arylmethylene-5(4H)-oxazolone Derivatives with Acylhydrazines

Kei Maekawa, Yoshitaka Kanno, Kanji Kubo, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

The ring-opening mode of the title oxazolones with acylhydrazines was investigated from both synthetic and mechanistic points of view. It was found that the novel ring-opening reaction proceeds to give 1,3,4-triazole-substituted (Z)-α-dehydroamino acids in high yields, irrespective of substituents and solvents examined. MM2 and PM5 calculations strongly suggested that the triazole ring is constructed via the preferential nucleophilic addition of the hydrazino nitrogen to the C–N double bond in the oxazolone ring.