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Russian Journal of Organic Chemistry

, Volume 47, Issue 11, pp 1738–1741 | Cite as

Synthesis of pyrrolidine and tetrahydroazonine derivatives from N-[bis(ethoxycarbonyl)methyl]tetrahydropyridinium bromide and methyl acetylenedicarboxylate

  • A. T. Soldatenkov
  • S. A. Soldatova
  • R. R. Suleimanov
  • K. B. Polyanskii
  • V. E. Kotsyuba
  • A. F. Smol’yakov
  • V. N. Khrustalev
  • M. Yu. Antipin
Article

Abstract

The reaction of N-methyl-N-(diethoxycarbonyl)methyltetrahydropyridinium bromide with dimethyl acetylenedicarboxylate in the presence of triethylamine at room temperature afforded 1,2-dimethyl 1-ethyl 2-[(3-vinyl-1-methyl-3-phenyl-2-ethoxycarbonyl)pyrrolidin-2-yl]-ethene-1,1,2-tricarboxylate in 25% yield. Its structure was proved by XRD analysis. At cooling to −20°C the pyrrolidine yield signifi cantly decreased and 3,4-dimethyl 2,2-diethyl 1-methyl-7-phenyl-1,5,8,9-tetrahydro-2H-azonine-2,2,3,4-tetratcarboxylate was obtained in 31% yield.

Keywords

Pyrrolidine Quaternary Salt Ethenyl Acetylenedicarboxylate DMAD 
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

© Pleiades Publishing, Ltd. 2011

Authors and Affiliations

  • A. T. Soldatenkov
    • 1
  • S. A. Soldatova
    • 1
  • R. R. Suleimanov
    • 1
  • K. B. Polyanskii
    • 1
  • V. E. Kotsyuba
    • 1
  • A. F. Smol’yakov
    • 2
  • V. N. Khrustalev
    • 2
  • M. Yu. Antipin
    • 2
  1. 1.Russian University of Peoples FriendshipMoscowRussia
  2. 2.Nesmeyanov Institute of Organoelemental CompoundsRussian Academy of SciencesMoscowRussia

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