Regioselective Metal-free Decarboxylative Multicomponent Coupling of -Amino acids, Aldehydes and Isonitriles leading to N-substituted azacyclic-2-carboxamideswith Antithrombotic activity

Abstract

An atom-economical regioselective synthesis of N-substituted prolinamides or N-substituted pirperidine-2-carboxamides via a metal-free decarboxylative multicomponent coupling between L-proline or pipecolic acid, aldehydes and isonitriles is described. The cascade event involves sequential imine formation, decarboxylation, isonitrile insertion and hydrolysis to afford the product in one-pot. Two of the prolinamides were found to display appreciable antithrombotic activity via inhibition of platelet aggregation.