Three-Component Castagnoli-Cushman Reaction of 3-Arylglutaconic Acids with Aromatic Aldehydes and Amines Delivers Rare 4,6-Diaryl-1,6-dihydropyridin-2(3 H)-ones

Organic Letters
Andrei FirsovMikhail Krasavin

Abstract

Attempted use of 3-arylglutaconic acids in the three-component version of the Castagnoli-Cushman reaction with amines and aromatic aldehydes resulted in an unexpected formation of 4,6-diaryl 1,6-dihydropyridine-2(3 H)-ones. These are of interest as representatives of a rare heterocyclic chemotype for de novo biological investigation. Alternatively, these compounds can be oxidized into their 2-pyridone counterparts, stereoselectively reduced to give cis-configured 4,6-diaryl 2-piperidones, or isomerized to 5,6-dihydropyridin-2(1 H)-ones. All the three scaffolds are well represented in the bioactive compound domain.

References

Feb 9, 1973·The Journal of Organic Chemistry·M Cushman, N Castagnoli
Feb 2, 2013·Organic Letters·Nicolas GigantIsabelle Gillaizeau
Sep 28, 2013·Organic Letters·Ommidala PattawongPaul Ha-Yeon Cheong
Feb 28, 2014·Angewandte Chemie·Francesco Manoni, Stephen J Connon

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