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Regioselective Metal-Free Decarboxylative Multicomponent Coupling of α-Amino Acids, Aldehydes and Isonitriles Leading to N-Substituted Azacyclic-2-carboxamides with Antithrombotic Activity

Author:
Dighe, Shashikant U., K. S., Anil Kumar, Srivastava, Smriti, Shukla, Pankaj, Singh, Surendra, Dikshit, Madhu, Batra, Sanjay
Source:
Journal of organic chemistry 2015 v.80 no.1 pp. 99-108
ISSN:
1520-6904
Subject:
aldehydes, chemical structure, decarboxylation, hydrolysis, imines, organic chemistry, pipecolic acid, platelet aggregation, proline, regioselectivity
Abstract:
An atom-economical regioselective synthesis of N-substituted prolinamides or N-substituted piperidine-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.
Agid:
5503503