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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
journal contribution
posted on 2015-01-02, 00:00 authored by Shashikant U. Dighe, Anil Kumar K. S., Smriti Srivastava, Pankaj Shukla, Surendra Singh, Madhu Dikshit, Sanjay BatraAn
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.
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Regioselectivepipecolic acidAzacyclicplatelet aggregationAldehydedecarboxylationDecarboxylativeantithrombotic activityprolinamideregioselectivecascade eventActivityAnisonitrile insertionsequential imine formationaldehydedecarboxylativesynthesisAntithromboticpiperidinemulticomponentIsonitrileMulticomponenthydrolysisinhibitionAciddisplayAmino
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