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Iron-Catalyzed Synthesis of 2H-Imidazoles from Oxime Acetates and Vinyl Azides under Redox-Neutral Conditions

Zhongzhi Zhu, Xiaodong Tang, Jianxiao Li, Xianwei Li, Wanqing Wu, Guohua Deng and Huanfeng Jiang*

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

Z. Zhu, X. Tang, J. Li, X. Li, W. Wu, G. Deng, H. Jiang, Org. Lett., 2017, 19, 1370-1373.

DOI: 10.1021/acs.orglett.7b00203 (free Supporting Information)


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Abstract

An iron-catalyzed [3 + 2] annulation from readily available oxime acetates with vinyl azides enables the synthesis of 2,4-substituted 2H-imidazoles via N-O/N-N bond cleavages and two C-N bond formations. This green reaction involving oxime acetate as internal oxidant, acetic acid, and nitrogen as byproducts can be performed under mild reaction conditions and needs no additives or ligands.


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Key Words

N-heterocycles


ID: J54-Y2017