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

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

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2026, DOI: 10.1039/d6ob00476h

Authors

Vinokurov Andrey D. ¹ , Iliyasov Taygib M. ¹ , Karpenko Kirill A. ¹ , Krivoshchapov Nikolai V. ¹ , Ravcheev Fedor M. ^2,1 , Goloveshkin Alexander S. ³ , Elinson Michail N. ¹ , Vereshchagin Anatoly N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow, 119991, Russian Federation
2	Mendeleev University of Chemical Technology of Russia, Miusskaya Square 9, Moscow, 125047, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str., 28, Moscow, 119334, Russian Federation

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.

Vinokurov A.D. , Iliyasov T.M. , Karpenko K.A. , Krivoshchapov N.V. , Ravcheev F.M. , Goloveshkin A.S. , Elinson M.N. , Vereshchagin A.N.
The first thermal epimerization of 2-piperidinones and tetrahydropyridines in DMSO: synthesis, DFT calculations and NCI analysis
Organic & Biomolecular Chemistry. 2026. DOI: 10.1039/d6ob00476h WOS Scopus OpenAlex

Submitted:	Mar 23, 2026
Published print:	Oct 8, 2026

≡ Web of science:	WOS:001896831000001
≡ Scopus:	2-s2.0-105052762828
≡ OpenAlex:	W7220893081