Investigation of the stereochemistry of the [3.3]-sigmatropic rearrangement of the <i>sp</i>-isomer of 2-allylthio-5-acetyl-6-methyl-4-(2-nitrophenyl)-3-cyano-1,4-dihydropyridine

Authors

  • В. Н. Нестеров A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 117813
  • Л. А. Родиновская N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow
  • А. М. Шестопалов N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow
  • Ю. T. Стручков A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 117813

Abstract

The reaction of the syn-periplanar conformer (the sp-isomer) of morpholinium 5-acetyl-6-methyl-4-(2-nitrophenyl)-3-cyano-1,4-dihydropyridine-2-thiolate with allyl bromide proceeds regio- and stereoselectively with the formation of the sp-isomer of the substituted 2-allylthio-1,4-dihydropyridine. The [3.3]-sigmatropic rearrangement of the last leads to the sp-isomer of 3,4-trans-3-allyl-5-acetyl-6-methyl-4-(2-nitrophenyl)-3-cyano-1,2,3,4-tetrahydropyridine-2(1H)-thione.

How to Cite
Nesterov, V. N.; Rodinovskaya, L. A.; Shestopalov, A. M.; Struchkov, Yu. T. Chem. Heterocycl. Compd. 1997, 33, 557. [Khim. Geterotsikl. Soedin. 1997, 643.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02291939

Downloads

Published

1997-05-25

Issue

No. 5 (1997)

Section

Original Papers