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Two directions in the heterocyclization of thiocarbamoylpyridinium(isoquinolinium)ylides in their interaction with esters of acetylenecarboxylic acids

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Abstract

It has been found that pyridinium- and isoquinoliniumthiocarbamoylazomethinylides react with esters of acetylenedicarboxylic and propiolic acids in two directions. The first direction is heterocyclization of the thioamide fragment of the ylide; under the influence of dimethyl acetylenedicarboxylate, a thiazolyl-4-one ring is formed, and by the interaction of the pyridiniumylide with methyl propiolate, a thiazin-4-one ring is formed. The second direction consists of annelation of the imidazole ring to the isoquinoline system upon reaction with methyl propiolate.

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Authors and Affiliations

  1. Ural State Technical University - UPI, 620002, Ekaterinburg

    V. S. Berseneva, N. Yu. Biryucheva & V. A. Bakulev

Authors
  1. V. S. Berseneva
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  2. N. Yu. Biryucheva
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  3. V. A. Bakulev
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1688–1691, December, 1993.

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Berseneva, V.S., Biryucheva, N.Y. & Bakulev, V.A. Two directions in the heterocyclization of thiocarbamoylpyridinium(isoquinolinium)ylides in their interaction with esters of acetylenecarboxylic acids. Chem Heterocycl Compd 29, 1458–1461 (1993). https://doi.org/10.1007/BF00531412

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  • DOI: https://doi.org/10.1007/BF00531412

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