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Synthesis and Stereochemistry of 3-Hydroxy-1,2,3,6-tetrahydropyridines

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Abstract

A series of 1-benzyl-3-hydroxy-1,2,3,6-tetrahydropyridines, multipurpose synthons for fine organic synthesis and potential antiviral compounds, was prepared by the rearrangement of a number of 1-benzyl-3,4- epoxypiperidines under treatment with lithium amides. 3,4-Epoxypiperidines were obtained by oxidation of 1,2,5,6- tetrahydropyridines trifluoroacetates with a trifluoroperacetic acid. Convenient synthetic routes were found and developed. A conformation analysis of the series of stable 3,4-epoxypiperidines and 3-hydroxy-1,2,3,6- tetrahydropyridines was carried out.

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Authors and Affiliations

  1. Lomonosov Moscow State University, Moscow, 119992, Russia

    G. V. Grishina, A. A. Borisenko, I. S. Veselov & A. M. Petrenko

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  1. G. V. Grishina
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  2. A. A. Borisenko
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  3. I. S. Veselov
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  4. A. M. Petrenko
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 2, 2005, pp. 281–287.

Original Russian Text Copyright © 2005 by Grishina, Borisenko, Veselov, Petrenko.

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Grishina, G.V., Borisenko, A.A., Veselov, I.S. et al. Synthesis and Stereochemistry of 3-Hydroxy-1,2,3,6-tetrahydropyridines. Russ J Org Chem 41, 272–278 (2005). https://doi.org/10.1007/s11178-005-0156-4

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  • DOI: https://doi.org/10.1007/s11178-005-0156-4

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