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Issue 1, 2015
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Oxidative activation of dihydropyridine amides to reactive acyl donors

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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.

Graphical abstract: Oxidative activation of dihydropyridine amides to reactive acyl donors

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Supplementary files

Article information


Submitted
11 Sep 2014
Accepted
09 Oct 2014
First published
31 Oct 2014

Org. Biomol. Chem., 2015,13, 185-198
Article type
Paper
Author version available

Oxidative activation of dihydropyridine amides to reactive acyl donors

E. D. Funder, J. B. Trads and K. V. Gothelf, Org. Biomol. Chem., 2015, 13, 185
DOI: 10.1039/C4OB01931H

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