The first thermal epimerization of 2-piperidinones and tetrahydropyridines in DMSO: synthesis, DFT calculations and NCI analysis.

Authors

Andrey D Vinokurov, Taygib M Iliyasov, Kirill A Karpenko, Nikolai V Krivoshchapov, Fedor M Ravcheev, Alexander S Goloveshkin, Michail N Elinson, Anatoly N Vereshchagin

Published in

Organic & biomolecular chemistry. Oct 08, 2026. Epub Oct 08, 2026.

Abstract

Research into the epimerization of piperidine-2-ones is exceedingly scarce. Blue light can induce epimerization of piperidine-2-ones, but this transformation necessitates the use of a blue LED and an iridium photocatalyst. We describe here the epimerization reactions of 2-piperidone-substituted pyridinium salts and 1,4,5,6-tetrahydropyridines in DMSO. The method is easy to perform and requires no catalysts or additional bases. An epimerization mechanism was proposed for each of these cases, and density functional theory (DFT) calculations were performed. With the aid of the noncovalent interaction (NCI) index, we were able to identify weak interactions within the molecule of a thermodynamically favorable epimer and compare them with those of a less thermodynamically favorable one.

PMID:
42845006
Bibliographic data and abstract were imported from PubMed on 08 Oct 2026.

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