Study on formation mechanism of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylic esters

Study on formation mechanism of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylic esters Научная публикация

Журнал

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

Вых. Данные

Год: 2022, Том: 71, Номер: 6, Страницы: 1278-1283 Страниц : 6 DOI: 10.1007/s11172-022-3531-1

Авторы

Karpenko K.A. ¹ , Iliyasov T.M. ¹ , Fakhrutdinov A.N. ¹ , Akulinin A.S. ¹ , Elinson M.N. ¹ , Vereshchagin A.N. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The mechanism of formation of methyl (4RS,6SR)-2-(4-bromophenyl)-5,5-dicyano-4,6-bis(4-methylphenyl)-1,4,5,6-tetrahydropyridine-3-carboxylate was estimated. Formation of 1,4,5,6-tetrahydropyridine moiety proceeds through a sequence of the Michael addition, the Mannich reaction, stereoselective cyclization to polysubstituted (2SR,3RS,4SR,6RS)-2-hydroxypiperidine, dehydration to (3RS,4SR,6RS)-3,4,5,6-tetrahydropyridine, and isomerization. Polysubstituted (4RS,6SR)-1,4,5,6-tetrahydropyridine was found to be thermodynamically more stable than isomeric (3RS,4SR,6RS)-3,4,5,6-tetrahydropyridine.

Karpenko K.A. , Iliyasov T.M. , Fakhrutdinov A.N. , Akulinin A.S. , Elinson M.N. , Vereshchagin A.N.
Study on formation mechanism of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylic esters
Russian Chemical Bulletin. 2022. V.71. N6. P.1278-1283. DOI: 10.1007/s11172-022-3531-1 WOS Scopus OpenAlex

Web of science:	WOS:000819001600023
Scopus:	2-s2.0-85133020090
OpenAlex:	W4283653024

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