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

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 subst...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-05, Vol.18 (2), p.3927-3937
Main Authors: Ravindran, Jaice, Yadhukrishnan, Velickakathu O, Asha, Reghuvaran S, Lankalapalli, Ravi S
Format: Article
Language:English
Subjects:
Amides
Crystallography
NMR
Nuclear magnetic resonance
Oxazole
Oxidation
Pyridinium
Substrates
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Summary: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 NaBH 4 is also observed. Multicomponent reactions (MCRs) using dienaminodioate with post-benzylic oxidative transformation mediated by DDQ that afforded a diverse array of products are described.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00721h