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A Metal-Free Three-Component Reaction of trans-β-Nitrostyrene Derivatives, Dibromo Amides, and Amines Leading to Functionalized Amidines

Meng Zhou, Jinlei Li, Chao Tian, Xiao Sun, Xiaoting Zhu, Yaohang Cheng, Guanghui An*, Guangming Li*

*School of Chemistry and Materials Science, Heilongjiang University, No. 74, Xuefu Road, Nangang District, Harbin 150080, People’s Republic of China, Email:,

M. Zhou, J. Li, C. Tian, X. Sun, X. Zhu, Y. Cheng, G. An, G. Li, J. Org. Chem., 2019, 84, 1015-1024.

DOI: 10.1021/acs.joc.8b02998

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A mild, metal-free, multicomponent reaction provides N-acyl amidines from nitroalkene derivatives, dibromo amides, and amines via formation of an initial α,α-dibromonitroalkane intermediate that can undergo C-C bond cleavage. This alternative approach toward N-acyl amidines enables rapid construction of amidine frameworks with high diversity and complexity.

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Key Words

amidines (C=N, C-N), multicomponent reactions

ID: J42-Y2019