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Issue 20, 2020
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Dienaminodioate based multicomponent reactions with post-benzylic oxidative transformations mediated by DDQ

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Abstract

Multicomponent reactions (MCRs) using dienaminodioate with post-benzylic oxidative transformation mediated by DDQ that afforded a diverse array of products are described. An unprecedented rearrangement of 1,2-dihydropyridines (1,2-DHPs), 3CR products, to 2-pyridones in good yields with a broad substrate scope by DDQ-mediated benzylic oxidation via a pyridinium intermediate is reported. Treatment of the pyridinium intermediate with tert-butyl isocyanide afforded isomerized 1,2-DHPs, analogous to Ritter amides. Further diversification using 3CR products bearing a benzylic group, predictably, promoted the synthesis of 2-pyridone with a benzylideneamine group and a benzo[d]oxazole appended biaryl group by DDQ. A formal 1,6-reduction product from 2-pyridone in the presence of NaBH4 is also observed.

Graphical abstract: Dienaminodioate based multicomponent reactions with post-benzylic oxidative transformations mediated by DDQ

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Supplementary files

Article information


Submitted
06 Apr 2020
Accepted
06 May 2020
First published
06 May 2020

Org. Biomol. Chem., 2020,18, 3927-3937
Article type
Paper

Dienaminodioate based multicomponent reactions with post-benzylic oxidative transformations mediated by DDQ

J. Ravindran, V. O. Yadhukrishnan, R. S. Asha and R. S. Lankalapalli, Org. Biomol. Chem., 2020, 18, 3927
DOI: 10.1039/D0OB00721H

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