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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 1979–1989 | Cite as

Stereoselective one-pot synthesis of polycyanosubstituted piperidines

  • Anatoly N. Vereshchagin
  • Kirill A. Karpenko
  • Michail N. Elinson
  • Sergey V. Gorbunov
  • Alexandra M. Gordeeva
  • Pavel I. Proshin
  • Alexander S. Goloveshkin
  • Mikhail P. Egorov
Original Paper
  • 91 Downloads

Abstract

An effective and facile multicomponent method for the synthesis of polysubstituted piperidines is described. The Michael–Mannich type cascade of benzylidenemalononitriles with aromatic aldehydes and ammonium acetate or aqueous ammonia provides convenient access to the stereoselective synthesis of 3,3,5,5-tetracyano-2,4,6-triarylpiperidines in good to excellent yields in one-pot manner. Ammonium acetate or aqueous ammonia plays a role both as a catalyst and as a nitrogen source. It is established that the reaction proceeds via sequence of equilibriums and a competitive mechanisms are implemented.

Graphical abstract

Keywords

Multicomponent reaction Polysubstituted piperidines Aromatic aldehydes Benzylidenemalononitriles Stereoselectivity 

Notes

Acknowledgements

This work was supported by the Russian Science Foundation (RSF Grant 17-73-20260).

Supplementary material

706_2018_2187_MOESM1_ESM.docx (6.1 mb)
Supplementary material 1 (DOCX 6292 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Anatoly N. Vereshchagin
    • 1
  • Kirill A. Karpenko
    • 1
  • Michail N. Elinson
    • 1
  • Sergey V. Gorbunov
    • 1
  • Alexandra M. Gordeeva
    • 1
  • Pavel I. Proshin
    • 1
  • Alexander S. Goloveshkin
    • 2
  • Mikhail P. Egorov
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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