Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines

Autor:	Ivan E. Ushakov, Michail N. Elinson, Anatoly N. Vereshchagin, Vladimir A. Smirnov, Taygib M. Iliyasov, Kirill A. Karpenko
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Organic Chemistry Michael reaction Diastereomer Organic chemistry Stereoselectivity Methanol Ammonium acetate Mannich reaction Alkyl Stereocenter
Zdroj:	Chemistry of Heterocyclic Compounds. 57:929-933
ISSN:	1573-8353 0009-3122
Popis:	A novel four-component diastereoselective synthesis of polysubstituted tetrahydropyridines is reported. The Michael addition – Mannich reaction – cyclization – dehydration cascade of benzylidenemalononitriles, esters of 3-oxocarboxylic acids, aromatic aldehydes, and ammonium acetate in methanol provides convenient access to 2-substituted alkyl (4SR,6RS)-4,6-diaryl-5,5-dicyano-1,4,5,6-tetrahydropyridine- 3-carboxylates with two stereocenters in 66–92% yields. The formation of products was highly stereoselective, with only one diastereomer formed. Ammonium acetate plays 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 spectral studies. The formation of single diastereomer was confirmed by singe crystal X-ray diffraction studies.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3ff2ec58366ec8a4218e90a2ce60079e https://doi.org/10.1007/s10593-021-03002-5 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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