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Issue 21, 2015
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Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines

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Abstract

A wide range of 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives were synthesized in good to excellent yields from 1,3-diarylated/heterylated-2-propen-1-ones (chalcones) in one pot under metal and base-free conditions. This domino reaction suggests a novel mechanism comprising of Michael addition followed by amination, subsequent intramolecular amidation and finally dehydronitrosation. The usefulness of the designed 4,6-diarylated/heterylated pyridin-2(1H)-one derivatives has further been demonstrated by synthesizing medicinally important 2,4,6-triaryl/heteryl pyridines via Pd-catalyzed cross-coupling reaction.

Graphical abstract: Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines

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Article information


Submitted
18 Mar 2015
Accepted
14 Apr 2015
First published
14 Apr 2015

Org. Biomol. Chem., 2015,13, 5944-5954
Article type
Paper
Author version available

Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines

R. Khajuria, P. Kannaboina, K. K. Kapoor, A. Gupta, G. Raina, A. K. Jassal, L. K. Rana, M. S. Hundal and P. Das, Org. Biomol. Chem., 2015, 13, 5944
DOI: 10.1039/C5OB00545K

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