Synergetic copper/zinc catalysis: synthesis of aryl/heteroaryl-fused 1H-pyrrolo[3,2-c]pyridines?

Chemical Communications Pub Date: 2022-01-07 DOI: 10.1039/D1CC05514C

Abstract

Scaffolds having a 1H-pyrrolo[3,2-c]pyridine core show significant biological activity. Herein, we report a synergetic copper/zinc-catalyzed one-step annulation reaction of 2-amino (hetero)arylnitriles with ynamide-derived buta-1,3-diynes to deliver 1H-pyrrolo[3,2-c]quinoline-2,4-diamine derivatives in moderate to good yields. The annulation reaction follows a double cyclization pathway. The gram-scale synthesis of 1H-pyrrolo[3,2-c]quinoline-2,4-diamine proves the practicality of this protocol.

Graphical abstract: Synergetic copper/zinc catalysis: synthesis of aryl/heteroaryl-fused 1H-pyrrolo[3,2-c]pyridines
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