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Intramolecular N to N acyl migration in conformationally mobile 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinoline] systems promoted by debenzylation conditions (HCOONH4/Pd/C)

  • Research Article
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Central European Journal of Chemistry

Abstract

We report an efficient and useful synthesis of new attractive spiropiperdine scaffolds 4 based on an intramolecular acyl transfer process in 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 3 using simple and mild debenzylation reaction conditions (HCOONH4/Pd/C). The compounds 3 were prepared by acylating 1-benzyl-4′-methyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 2 that are easily available from 1-benzyl-4-piperidone 1. The intramolecular character of this process was proven primarily through a crossover experiment technique. Through an examination of all spectroscopic information (1H, 13C NMR, VT-1H NMR, and 2D NMR) it was possible to correctly predict amide configurations and piperidine ring conformations of starting and final spiropiperidine compounds.

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Authors and Affiliations

  1. Environmental Research Group, Environmental Chemistry Faculty, Santo Tomas University, A.A. 1076, Bucaramamga, Colombia

    Leonor Y. Vargas Méndez

  2. Laboratory of Organic & Biomolecular Chemistry, School of Chemistry, Industrial University of Santander, A.A. 678, Bucaramamga, Colombia

    Vladimir V. Kouznetsov

Authors
  1. Leonor Y. Vargas Méndez
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  2. Vladimir V. Kouznetsov
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Correspondence to Vladimir V. Kouznetsov.

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Méndez, L.Y.V., Kouznetsov, V.V. Intramolecular N to N acyl migration in conformationally mobile 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinoline] systems promoted by debenzylation conditions (HCOONH4/Pd/C). cent.eur.j.chem. 9, 877–885 (2011). https://doi.org/10.2478/s11532-011-0082-y

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