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Paper | Regular issue | Vol 85, No. 2, 2012, pp.313-331
Published online, 10th January, 2012
DOI: 10.3987/COM-11-12372
Scope and Limitations of a Modified Hantzsch Reaction for the Synthesis of Oxazole-Dehydroamino Acid Derivatives from Dehydroamino Acid Amides

Akihiro Nagaya, Yoji Yamagishi, Yasuchika Yonezawa, Shoji Akai,* Chung-gi Shin, and Ken-ichi Sato*

*Department of Material & Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

A variety of oxazole derivatives that possess an α,β-unsaturated substituent at the 2-position were conveniently synthesized in good yields via a Hantzsch-type reaction between dehydroamino acid amides and β-bromopyruvate derivatives. Furthermore, oxazoles with substituents at the 2- and 5-positions were also obtained in good yields using the corresponding β-substituted β-bromopyruvate derivatives. A revised reaction mechanism to explain the enhanced reactivity of dehydroamino acid amides for the Hantzsch-oxazole-type reaction is presented.