SYNTHESIS OF PYRROLIDINES AND TETRAHYDRO-1H-AZEPINES FROM 4-ARYL-1-BENZOYL(ETHOXYCARBONYL)METHYL-1-METHYL-1,2,3,6-TETRAHYDROPYRIDINIUM HALIDES

Authors

  • С. А. Солдатова People's Friendship University of Russia, Moscow 117198
  • Г. С. Гимранова People's Friendship University of Russia, Moscow 117198
  • Ж. А. Мамырбекова People's Friendship University of Russia, Moscow 117198
  • К. Б. Полянский People's Friendship University of Russia, Moscow 117198
  • С. В. Акбулатов People's Friendship University of Russia, Moscow 117198
  • А. Т. Солдатенков People's Friendship University of Russia, Moscow 117198

DOI:

https://doi.org/10.1007/7340

Keywords:

4-aryl-1-benzoyl(ethoxycarbonyl)methyl-1, 2, 3, 6-tetrahydropyridinium halides, N-ylides, pyrollidines, tetrahydro-1H-azepines, 1, 2-shift, sigmatropic rearrangement

Abstract

4-Aryl-1,2,3,6-tetrahydropyridinium quaternary salts which have a benzoylmethyl or ethoxycarbonylmethyl group on atom N-1 generate N-ylides when heated in the presence of NaH and they can rearrange in situ with contraction or  expansion of the six-membered heterocycle to give substituted pyrrolidines (as a result of a [2,3]-sigmatropic rearrangement) or 1H-tetrahydroazepine derivatives (via Stevens rearrangement). The presence of an aryl substituent at position C-4 in the tetrahydropyridine ring allows to avoid the formation of elimination products and changes the direction of the reaction towards the preparation of the tetrahydroazepines.

How to Cite
Soldatova, S. A.; Gimranova, G. S.; Mamyrbekova, Zh. A.; Polyanskii, K. B.; Akbulatov, S. V.; Soldatenkov, A. T.  Chem. Heterocycl. Compd. 2007, 43, 1420. [Khim. Geterotsikl. Soedin. 2007, 1670.]

For this article in the English edition see DOI 10.1007/s10593-007-0219-2


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Published

2023-01-20

Issue

No. 11 (2007)

Section

Original Papers