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Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 15. Isomerization of thiazolo[4,5-b]quinoxalines in the presence of acids

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

4-Alkyl-2-phenyl-3a,4,9,9a-tetrahydrothiazolo[4,5-b]quinoxalines undergo isomerization in chloroform in the presence of acids to the regioisomeric (with respect to them) 9-alkyl-substituted derivatives. Under the same conditions 2,4-dimethyl-3a,4-9,9a-tetrahydrothiazolo [4,5-b]quinoxaline undergoes isomerization to 4-methyl-1H-2,3,3a,4,9,9a-hexahydropyrrolo[2,3-b]quinoxaline-2-thione. It was demonstrated by means of deuterium labels that in both cases the isomerization proceeds through a step involving dissociation to a quinoxalinium cation and the corresponding thioamide.

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Authors and Affiliations

  1. S. M. Kirov Ural Polytechnic Institute, 620002, Sverdlovsk

    V. N. Charushin, V. G. Baklykov, O. N. Chupakhin & V. N. Drozd

Authors
  1. V. N. Charushin
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  2. V. G. Baklykov
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  3. O. N. Chupakhin
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  4. V. N. Drozd
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Additional information

See [1] for Communication 14.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 396–403, March, 1985.

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Charushin, V.N., Baklykov, V.G., Chupakhin, O.N. et al. Cyclization of N-alkylazinium cations with bifunctional nucleophiles. 15. Isomerization of thiazolo[4,5-b]quinoxalines in the presence of acids. Chem Heterocycl Compd 21, 331–338 (1985). https://doi.org/10.1007/BF00506677

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  • DOI: https://doi.org/10.1007/BF00506677

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