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Highly diastereoselective synthesis of pyridinium-substituted piperidin-2-ones from pyridinium ylides, aldehydes, Michael acceptors, and ammonium acetate Научная публикация

Журнал Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122
Вых. Данные Год: 2024, Том: 59, Страницы: 778-785 Страниц : 8 DOI: 10.1007/s10593-024-03271-w
Авторы Vinokurov Andrey D. 1 , Iliyasov Taygib M. 1 , Karpenko Kirill A. 1 , Akchurin Radmir N. 1 , Derkach Yana V. 1 , Vereshchagin Anatoly N. 1
Организации
1 N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky Ave., Moscow, 119334, Russia

Реферат: A novel four-component diastereoselective synthesis of piperidin-2-one salts containing a quaternized pyridine unit is reported. The Michael–Mannich cascade was conducted using Michael acceptors, pyridinium ylides, aromatic aldehydes, and ammonium acetate in methanol. It is a convenient approach to the synthesis of 1-((3SR,4RS,6SR)-4,6-diaryl-5,5-dicyano-2-oxopiperidin-3-yl)pyridin-1-ium halides with three stereocenters in 48–84% yield or 1-[(3SR,4RS,5RS,6SR)-4,6-diaryl-5-cyano-5-(methoxycarbonyl)-2-oxopiperidin-3-yl]-pyridin-1-ium halides with four stereocenters in 44–74%. This reaction is highly stereoselective. Only one diastereomer was formed. Ammonium acetate plays a dual role, acting as a base and as a nitrogen source. Structures of the synthesized compounds were confirmed by 1H, 13C NMR, IR, and mass spectra. The formation of a single diastereomer was confirmed by singe crystal X-ray diffraction studies. Products were obtained by simple filtration, and other purification methods as column chromatography were not necessary.
Библиографическая ссылка: Vinokurov A.D. , Iliyasov T.M. , Karpenko K.A. , Akchurin R.N. , Derkach Y.V. , Vereshchagin A.N.
Highly diastereoselective synthesis of pyridinium-substituted piperidin-2-ones from pyridinium ylides, aldehydes, Michael acceptors, and ammonium acetate
Chemistry of Heterocyclic Compounds. 2024. V.59. P.778-785. DOI: 10.1007/s10593-024-03271-w WOS OpenAlex
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Web of science: WOS:001142075700001
OpenAlex: W4390810700
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