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

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

Journal

Chemistry of Heterocyclic Compounds
ISSN: 1573-8353 , E-ISSN: 0009-3122

Output data

Year: 2021, Volume: 57, Number: 9, Pages: 929-933 Pages count : 5 DOI: 10.1007/s10593-021-03002-5

Authors

Vereshchagin Anatoly N. ¹ , Iliyasov Taygib M. ¹ , Karpenko Kirill A. ¹ , Smirnov Vladimir A. ^1,2 , Ushakov Ivan E. ³ , Elinson Michail N. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russia
2	Mendeleev University of Chemical Technology of Russia
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia

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.

Vereshchagin A.N. , Iliyasov T.M. , Karpenko K.A. , Smirnov V.A. , Ushakov I.E. , Elinson M.N.
Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines
Chemistry of Heterocyclic Compounds. 2021. V.57. N9. P.929-933. DOI: 10.1007/s10593-021-03002-5 WOS Scopus OpenAlex

Web of science:	WOS:000702194300003
Scopus:	2-s2.0-85116144068
OpenAlex:	W3202322298

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OpenAlex	7
Scopus	7
Web of science	7