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Methylation of 2-amino-δ2-thiazolin-4-one

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that the nucleophilicity of the sodium salt of 2-amino-Δ2-thiazolin-4-one with respect to dimethyl sulfate and methyl iodide is extremely low, regardless of the nature of the solvent. The anomalous (in the 4-thiazolidone series) behavior of this salt in methylation is explained by the low degree of heterolytic dissociation of the O-Na bond. The possible reasons for the inertness of the oxygen atom in the anions of 2-substituted 4-thiazolidones with respect to alkylating agents are discussed.

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Authors and Affiliations

  1. Lensovet Leningrad Technological Institute, 198013, Leningrad

    Yu. G. Basova, S. M. Ramsh & A. I. Ginak

Authors
  1. Yu. G. Basova
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  2. S. M. Ramsh
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  3. A. I. Ginak
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1046–1049, August, 1981.

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Basova, Y.G., Ramsh, S.M. & Ginak, A.I. Methylation of 2-amino-δ2-thiazolin-4-one. Chem Heterocycl Compd 17, 773–776 (1981). https://doi.org/10.1007/BF00503655

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  • DOI: https://doi.org/10.1007/BF00503655

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