Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles

Xiaodong Tang, Zhongzhi Zhu, Chaorong Qi, Wanqing Wu and Huanfeng Jiang*

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China, Email: jianghfscut.edu.cn

X. Tang, Z. Zhu, C. Qi, W. Wu, H. Jiang, Org. Lett., 2016, 18, 180-183.

DOI: 10.1021/acs.orglett.5b03188

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Abstract

A copper-catalyzed coupling of oxime acetates with isothiocyanates provides various 4-substituted and 4,5-disubstituted 2-aminothiazoles under mild reaction conditions via copper-catalyzed N-O bond cleavage, activation of vinyl sp² C-H bonds, and C-S/C-N bond formations. The oxime acetates serve not only as substrate but also as single oxidant.

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Key Words

thiazoles

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ID: J54-Y2016