Highly diastereoselective synthesis of piperidine-2-one-substituted pyridinium salts from pyridinium ylides, aldehydes, Michael acceptors and ammonium acetate DOI Creative Commons
Andrey Vinokurov, Taygib M. Iliyasov, Kirill A. Karpenko

и другие.

Research Square (Research Square), Год журнала: 2023, Номер unknown

Опубликована: Июль 13, 2023

Abstract A novel four-component diastereoselective synthesis of pyridinium salts piperidin-2-ones is reported. The Michael–Mannich cascade was conducted using Michael acceptors, ylides, aromatic aldehydes and ammonium acetate in methanol. It a convenient approach to the 1-((3 SR ,4 RS ,6 )-5,5-dicyano-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenides with three stereocenters 48–84% or 1-(( 3SR,4RS,5RS,6SR )-5-cyano-5-(methoxycarbonyl)-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenide four 44–74%. This reaction highly stereoselective. Only one diastereomer formed. Ammonium plays dual role, acting as base nitrogen source. Structures synthesized compounds were confirmed by 1 H NMR, 13 C IR mass spectra. formation single singe-crystal X-ray diffraction studies.

Язык: Английский

The Design, Synthesis, and Antibacterial Activity of Ferrocene-Based Long-Chain Quaternary Ammonium Salts DOI
Cynthia Y. Yan,

Ji-Bin Zhuo,

Yanhou Geng

и другие.

Опубликована: Янв. 1, 2024

Язык: Английский

Процитировано

0
Highly diastereoselective synthesis of piperidine-2-one-substituted pyridinium salts from pyridinium ylides, aldehydes, Michael acceptors and ammonium acetate DOI Creative Commons
Andrey Vinokurov, Taygib M. Iliyasov, Kirill A. Karpenko

и другие.

Research Square (Research Square), Год журнала: 2023, Номер unknown

Опубликована: Июль 13, 2023

Abstract A novel four-component diastereoselective synthesis of pyridinium salts piperidin-2-ones is reported. The Michael–Mannich cascade was conducted using Michael acceptors, ylides, aromatic aldehydes and ammonium acetate in methanol. It a convenient approach to the 1-((3 SR ,4 RS ,6 )-5,5-dicyano-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenides with three stereocenters 48–84% or 1-(( 3SR,4RS,5RS,6SR )-5-cyano-5-(methoxycarbonyl)-2-oxo-4,6-diarylpiperidin-3-yl)pyridin-1-ium halogenide four 44–74%. This reaction highly stereoselective. Only one diastereomer formed. Ammonium plays dual role, acting as base nitrogen source. Structures synthesized compounds were confirmed by 1 H NMR, 13 C IR mass spectra. formation single singe-crystal X-ray diffraction studies.

Язык: Английский

Процитировано

0