Stereoselective synthesis and structure of 3,4-<i>trans</i>-6-amino-4-aryl-3-carbamoyl-5-cyano-1,2,3,4-tetrahydropyridin-2(1H)-thiones

Abstract

Condensation of thiocarbamoylacetamide with arylidenemalononitrile or the three-component condensation of thiocarbamoylacetamide with aldehydes and malononitrile in the presence of triethylamine occurred regioselectively to give triethylammonium-6-amino-4-aryl-3-carbamoyl-5-cyano-1,4-dihydropyridine-2-thiolates. Protonation of the latter occurred stereoselectively to give 3,4-trans-6-aryl-3-carbamoyl-5-cyano-1,2,3,4-tetrahydropyridin-2(1H)-thiones. The¹H NMR spectrum and single X-ray crystallography indicate that the dihydropyridine ring has he sofa conformation with trans-pseudodiaxial orientation of the Ar and CONH₂ groups and trans-pseudoequatorial orientation of atoms 3-H and 4-H.

How to Cite
Rodinovskaya, L. A.; Shestopalov, A. M.; Nesterov, V. N. Chem. Heterocycl. Compd. 1996, 32, 1182. [Khim. Geterotsikl. Soedin. 1996, 1376.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169231