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

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JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 12, 页码 6102-6108

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00614

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  1. ICSN
  2. CNRS

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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 center dot 2H(2)O, 2,2'-bipyridine, and an O-2 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.

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