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

J Org Chem

Key Laboratory of Functional Inorganic Material Chemistry (MOE), School of Chemistry and Materials Science , Heilongjiang University, No. 74, Xuefu Road , Nangang District, Harbin 150080 , People's Republic of China.

Published: January 2019

A mild, metal-free, and multicomponent route for the preparation of N-acyl amidines from nitroalkene derivatives, dibromo amides, and amines has been developed that accesses an initial α,α-dibromonitroalkane intermediate that can undergo C-C bond cleavage. This protocol offers an alternative approach toward N-acyl amidines and features the rapid construction of amidine frameworks with high diversity and complexity. The procedure also accesses bisamidine and α,β-unsaturated amidines which are challenging targets by traditional methods.

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http://dx.doi.org/10.1021/acs.joc.8b02998DOI Listing

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