Rhodium-Catalyzed [4 + 2]-Annulation of o-Acylanilines with N-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines.

Abstract

Efficient synthesis of 3-aminoquinolines has been demonstrated from readily accessible N-sulfonyl-1,2,3-triazoles and o-acylaniline derivatives. This transformation involves the generation of C-C and C-N bonds through insertion of rhodium azavinyl carbenoid into a N-H bond followed by cyclization and aromatization. The important features include good functional group tolerance, synthesis of indoloquinoline, and isolation of N-H-inserted product, a potential intermediate.