One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones

One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 5, Pages: 1261-1272 Pages count : 12 DOI: 10.1007/s11172-024-4242-6

Authors

Vinokurov A.D. ¹ , Iliyasov T.M. ¹ , Karpenko K.A. ¹ , Valeev A.B. ¹ , Fakhrutdinov A.N. ¹ , Elinson M.N. ¹ , Vereshchagin A.N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119334, Moscow, Russian Federation

The present study describes a multicomponent synthesis of pyridinium derivatives of piperidin-2-ones from aromatic aldehydes, malononitriles, pyridines, haloacetates, and ammonium acetate. The synthesis occurs through the in situ formation of pyridinium ylide and involves the Knoevenagel—Michael—Mannich cyclization cascade. 1-[(3RS,4SR,6RS)-4,6-Diaryl-5,5-dicyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with three stereocenters and 1-[(3RS,4SR,5SR,6RS)-5-alkoxycarbonyl-4,6-diaryl-5-cyano-2-oxopiperidin-3-yl]pyridin-1-ium halides with four stereocenters were synthesized.

Vinokurov A.D. , Iliyasov T.M. , Karpenko K.A. , Valeev A.B. , Fakhrutdinov A.N. , Elinson M.N. , Vereshchagin A.N.
One-pot formation of six bonds: pseudo-six-component diastereoselective synthesis of pyridinium-containing piperidin-2-ones
Russian Chemical Bulletin. 2024. V.73. N5. P.1261-1272. DOI: 10.1007/s11172-024-4242-6 WOS Scopus OpenAlex

Web of science:	WOS:001252371600040
Scopus:	2-s2.0-85196483631
OpenAlex:	W4399899442

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