Development of β,β-Dibrominated Secondary Enamides and Their Application to the Synthesis of 5-Br Oxazoles

Jun Ma, Qijie Zou, Chunhua Wang*, Guangwei Yin and Fangyi Li*

*Foshan University, Foshan 528225; Tianjin University of Traditional Chinese Medicine, Tianjin 301617, P. R. China, Email: pharmwch126.com, lifangyitjutcm.edu.cn

J. Ma, Q. Zou, C. Wang, G. Yin, F. Li, J. Org. Chem., 2022, 87, 15670-15678.

DOI: 10.1021/acs.joc.2c01927

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Abstract

A base-promoted dibromination of enamides using CBr₄ as a bromine source provides β,β-dibrominated secondary enamides. These novel products can be readily transformed to 5-Br oxazoles via Cu(I) catalyzed intramolecular cyclization in good yields.

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proposed mechanisms

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Key Words

1,1-dibromoalkenes, oxazoles, carbon tetrabromide

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ID: J42-Y2022