Ag2O-promoted ring-opening reactions of cyclopropenones with oximes

Ye-Fei Yang; Xiao-Bo Huang; Wen-Xia Gao; Yun-Bing Zhou; Miao-Chang Liu; Hua-Yue Wu

doi:10.1039/D0OB00601G

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Ag₂O-promoted ring-opening reactions of cyclopropenones with oximes†

Ye-Fei Yang,^a Xiao-Bo Huang,

^a Wen-Xia Gao,

^a Yun-Bing Zhou,*^a Miao-Chang Liu

*^a and Hua-Yue Wu

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* Corresponding authors

^a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China
E-mail: zyb@wzu.edu.cn, mcl@wzu.edu.cn

Abstract

Ag₂O-promoted ring-opening reactions of cyclopropenones with oximes is disclosed in this work, providing a direct route to 1,3-oxazinones. This method highlights a new reactivity of cyclopropenones which undergo 1,4-addition with oximes followed by β-carbon elimination to in situ generate a α-carbonyl ketene intermediate.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/D0OB00601G
Article type: Communication
Submitted: 22 Mar 2020
Accepted: 14 Jul 2020
First published: 15 Jul 2020

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Org. Biomol. Chem., 2020,18, 5822-5825

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Ag₂O-promoted ring-opening reactions of cyclopropenones with oximes

Y. Yang, X. Huang, W. Gao, Y. Zhou, M. Liu and H. Wu, Org. Biomol. Chem., 2020, 18, 5822 DOI: 10.1039/D0OB00601G

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Organic & Biomolecular Chemistry