PAPER: Oxidative activation of dihydropyridine amides to reactive acyl donors

Funder ED, Trads JB, Gothelf KV.

Org Biomol Chem. 2015 Jan 7;13(1):185-98. doi: 10.1039/c4ob01931h.

Danish National Research Foundation, Center for DNA Nanotechnology, Department of Chemistry and iNANO, Gustav Wieds Vej 14, 8000 Aarhus C, Denmark. kvg@chem.au.dk.

Abstract

Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields.

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