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Regioselectivity and stereoselectivity of electrophilic quaternization of substituted 2-allyl(2-cyclohexen-1-yl)thionicotinic acids to thiazolo[3,2-a]pyridinium salts

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The electrophilic quaternization of substituted 2-allyl(2-cyclohexen-1-yl)-thionicotinic acids proceeds regioselectively and stereoselectively as a trans process with the formation of salts of 4a,10a-cis-4,4a-trans-1,2,3,4,4a,10a-hexahydrobenzothiazolo-[3,2-a]pyridinium acids. Trihalides of thiazolo[3,2-a]-pyridinium acids exist in equilibrium with their betaine form. The formation of betaines and reactions that proceed with a change in the anionic part of thiazolo[3,2-a]pyridinium salts have virtually no effect on the conformation of the heterocyclic cation.

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Authors and Affiliations

  1. T. G. Shevchenko Voroshilovgrad State Pedagogical Institute, 348011, Voroshilovgrad

    A. M. Shestopalov, L. A. Rodinovskaya, Yu. A. Sharanin & V. P. Litvinov

  2. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, 117913, Moscow

    A. M. Shestopalov, L. A. Rodinovskaya, Yu. A. Sharanin & V. P. Litvinov

Authors
  1. A. M. Shestopalov
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  2. L. A. Rodinovskaya
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  3. Yu. A. Sharanin
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  4. V. P. Litvinov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 256–263, February, 1990.

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Shestopalov, A.M., Rodinovskaya, L.A., Sharanin, Y.A. et al. Regioselectivity and stereoselectivity of electrophilic quaternization of substituted 2-allyl(2-cyclohexen-1-yl)thionicotinic acids to thiazolo[3,2-a]pyridinium salts. Chem Heterocycl Compd 26, 221–227 (1990). https://doi.org/10.1007/BF00499421

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  • DOI: https://doi.org/10.1007/BF00499421

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