Diastereoselective multicomponent synthesis of (4 RS ,6 SR )-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates

A. N. Vereshchagin; K. A. Karpenko; T. M. Iliyasov; M. N. Elinson; E. O. Dorofeeva; A. N. Fakhrutdinov; M. P. Egorov

doi:10.1007/s11172-018-2327-9

Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates

Authors: Vereshchagin A.N.¹, Karpenko K.A.¹, Iliyasov T.M.¹, Elinson M.N.¹, Dorofeeva E.O.¹, Fakhrutdinov A.N.¹, Egorov M.P.¹
Affiliations:
1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Issue: Vol 67, No 11 (2018)
Pages: 2049-2053
Section: Full Articles
URL: https://journals.rcsi.science/1066-5285/article/view/243174
DOI: https://doi.org/10.1007/s11172-018-2327-9
ID: 243174

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Abstract

Multicomponent reaction of benzylidenemalononitrile, 2-acetyl-3-arylacrylates, and aqueous ammonia in alcohols at room temperature proceeds stereoselectively to give (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates in 55–87% yields. In this reaction, ammonia acts as both the catalyst and the source of nitrogen for constructing tetrahydropyridine cycle.