Synthesis of Benzimidazo[2,1-<i>a</i>]isoquinoline and Indolo[2,1-<i>a</i>]isoquinoline Derivatives via Copper-Catalyzed Silylation/Methylation of 2-Arylindoles and 2-Arylbenzimidazoles
Pengbo Zhao, Youzhi Wang, Xiajun Wang, Daijiao Zhuang, Rulong Yan
Abstract
A one-pot method for the synthesis of silylsubstituted/methylsubstituted indolo[2,1-a]isoquinolin-6(5H)-ones and benzimidazo[2,1-a]isoquinoline-6(5H)-ones via copper(II)-initiated silylation/methylation of 2-arylindoles and 2-arylbenzimidazoles was developed. In this procedure, the C–Si bond and C–C bond were constructed by radical addition and cyclization. A series of 2-arylindole and 2-arylbenzimidazole derivatives were facilely transformed to indolo[2,1-a]isoquinolines and benzimidazo[2,1-a]isoquinolines in 39–83% yields.
Topics & Concepts
IsoquinolineChemistrySilylationMethylationCatalysisMedicinal chemistryCopperOrganic chemistryCombinatorial chemistryStereochemistryGeneBiochemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis