Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones

Qinghe Gao, Shan Liu, Xia Wu, Jingjing Zhang and Anxin Wu*

*Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China, Email: chwuaxmail.ccnu.edu.cn

Q. Gao, S. Liu, X. Wu, J. Zhang, A. Wu, Org. Lett., 2015, 17, 2960-2963.

DOI: 10.1021/acs.orglett.5b01241

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Abstract

In a direct annulation of hydrazides with methyl ketones for the synthesis of 1,3,4-oxadiazoles, the use of K₂CO₃ as a base achieves an unexpected and highly efficient C-C bond cleavage. This reaction is proposed to go through oxidative cleavage of Csp³-H bonds, followed by cyclization and deacylation.

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Key Words

1,3,4-oxadiazoles, iodine

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ID: J54-Y2015