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


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.


Bromide Organic Chemistry Allyl Morpholinium Dihydropyridine 
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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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