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Chemistry of Heterocyclic Compounds

, Volume 33, Issue 5, pp 557–565 | Cite as

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

  • V. N. Nesterov
  • L. A. Rodinovskaya
  • A. M. Shestopalov
  • Yu. T. Struchkov
Article
  • 46 Downloads

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.

Keywords

Bromide Organic Chemistry Allyl Morpholinium Dihydropyridine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • V. N. Nesterov
  • L. A. Rodinovskaya
  • A. M. Shestopalov
  • Yu. T. Struchkov

There are no affiliations available

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