Dighe Shashikant U, K S Anil Kumar, Srivastava Smriti, Shukla Pankaj, Singh Surendra, Dikshit Madhu, Batra Sanjay
Medicinal and Process Chemistry Division and Pharmacology Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, PO Box 173, Lucknow, 226031 Uttar Pradesh, India.
J Org Chem. 2015 Jan 2;80(1):99-108. doi: 10.1021/jo502029k. Epub 2014 Nov 26.
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.
