STEREOSELECTIVE SYNTHESIS AND ALKYLATION OF N-METHYLMORPHOLINIUM 4,5-<i>trans</i>-4-(2-CHLOROPHENYL)-3-CYANO-6-HYDROXY-5-(2-THENOYL)-6-TRIFLUOROMETHYL-1,4,5,6-TETRAHYDROPYRIDINE-2-THIOLATE. MOLECULAR AND CRYSTAL STRUCTURE OF 4,5-<i>trans</i>-4-(2-CHLOROPHENYL)-3-CYANO-6-HYDROXY-2-METHALLYLTHIO-5-(2-THENOYL)-6-TRIFLUOROMETHYL-1,4,5,6-TETRAHYDROPYRIDINE

Authors

  • С. Г. Кривоколыско Taras Shevchenko Lugansk State Pedagogical University, Lugansk 91011
  • В. Д. Дяченко Taras Shevchenko Lugansk State Pedagogical University, Lugansk 91011
  • А. Н. Чернега Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev
  • В. П. Литвинов N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow

Keywords:

2-thenoyltrifluoroacetone, tetrahydropyridines, 2-chlorobenzaldehyde, cyanothioacetamide, alkylation, condensation

Abstract

The condensation of 2-chlorobenzaldehyde with cyanothioacetamide and 2-thenoyltrifluoroacetone in the presence of N-methylmorpholine takes place stereoselectively and leads to the formation of N‑methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine-2-thiolate. The latter was used to synthesize the corresponding 2‑alkylthiotetrahydropyridines. The structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-2-methallylthio-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine was determined by X-ray crystallographic analysis.

How to Cite
Krivokolysko, S. G.; Dyachenko, V. D.; Chernega, A. N.; Litvinov, V. P. Chem. Heterocycl. Compd. 2001, 37, 1208. [Khim. Geterotsikl. Soedin. 2001, 1324.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1013889208646

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Published

2001-10-25

Issue

No. 10 (2001)

Section

Original Papers