Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines

2015/06/09 by Lam Quang Tran, Jihui Li, Luc Neuville · 26 citations
Chemistry · #Aryl #Asymmetric Hydrogenation and Catalysis #Catalysis #Catalytic C–H Functionalization Methods #Chemistry #Combinatorial chemistry #Component (thermodynamics) #Copper #Domino #Medicinal chemistry #Organic chemistry #Polymer chemistry #Quinazolinone synthesis and applications #Surface modification

paper · doi:10.1021/acs.joc.5b00614

published in The Journal of Organic Chemistry 80(12), 6102-6108 (American Chemical Society)

openalex publication_date 2015/06/09 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

A copper-promoted three-component synthesis of 2-aminobenzimidazoles (1) or of 2-aminoquinazolines (2) involving cyanamides, arylboronic acids, and amines has been developed. The operationally simple oxidative process, performed in the presence of K2CO3, a catalytic amount of CuCl2·2H2O, 2,2'-bipyridine, and an O2 atmosphere (1 atm), allows the rapid assembly of either benzimidazoles or quinazolines starting from aryl- or benzyl-substituted cyanamides, respectively. In this process, the copper promotes the formation of three bonds, two C-N bonds, and an additional bond resulting from C-H functionalization event.

Cited by

• A Simple and Efficient Approach for the Synthesis of 2-Aminated Quinazoline Derivatives via Metal Free Oxidative Annulation. [europepmc]
• Recent Advances in Metal-Catalyzed Approaches for the Synthesis of Quinazoline Derivatives. [europepmc]

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