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Stereoselective one-pot synthesis of polycyanosubstituted piperidines

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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.

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Acknowledgements

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

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

    Anatoly N. Vereshchagin, Kirill A. Karpenko, Michail N. Elinson, Sergey V. Gorbunov, Alexandra M. Gordeeva, Pavel I. Proshin & Mikhail P. Egorov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation

    Alexander S. Goloveshkin

Authors
  1. Anatoly N. Vereshchagin
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  2. Kirill A. Karpenko
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  3. Michail N. Elinson
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  4. Sergey V. Gorbunov
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  5. Alexandra M. Gordeeva
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  6. Pavel I. Proshin
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  7. Alexander S. Goloveshkin
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  8. Mikhail P. Egorov
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Correspondence to Anatoly N. Vereshchagin.

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Vereshchagin, A.N., Karpenko, K.A., Elinson, M.N. et al. Stereoselective one-pot synthesis of polycyanosubstituted piperidines. Monatsh Chem 149, 1979–1989 (2018). https://doi.org/10.1007/s00706-018-2187-x

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  • DOI: https://doi.org/10.1007/s00706-018-2187-x

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