Rhodium-Catalyzed [4 + 2]-Annulation of <i>o</i>-Acylanilines with <i>N</i>-Sulfonyl-1,2,3-triazoles: Synthesis of 3-Aminoquinolines
Kavuri Rupa, Dongari Yadagiri, Pazhamalai Anbarasan
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.
Topics & Concepts
AnnulationCarbenoidRhodiumSulfonylChemistryAromatizationCatalysisMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryAlkylCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis