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Base-Induced Transformation of 2-Acyl-3-alkyl-2H-azirines to Oxazoles: Involvement of Deprotonation-Initiated Pathways

Yingtang Ning, Yuko Otani and Tomohiko Ohwada*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: ohwadamol.f.u-tokyo.ac.jp

Y. Ning, Y. Otani, T. Ohwada, J. Org. Chem., 2017, 82, 6313-6326.

DOI: 10.1021/acs.joc.7b00904 (free Supporting Information)


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Abstract

A base-induced transformation reaction of 2-acyl-3-alkyl-2H-azirines provides oxazoles via a deprotonation-initiated mechanism followed by nucleophilic addition to the imine functionality. Intermediacy of ketenimine is consistent with both experimental and computational results, at least under strongly basic reaction conditions.

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Key Words

Oxazoles


ID: J42-Y2017