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Six-membered cyclic semiaminal as intermediate in the synthesis of thiazoles from thiosemicarhazide and α-haloketones

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Abstract

Cyclization of thiosemicarbazide with methyl 3-chloro-2-oxo-3-phenylpropionate in MeCN results in 5-hydroxy-2-imino-5-methoxycarbonyl-6-phenylperhydro-1,3,4-thiadiazine. The structure of the product has been confirmed using spectral (IR,1H,13C,13C{1H} NMR) methods and chemical transformations.

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Authors and Affiliations

  1. A.E.Arbusov Institute of Organic and Physical Chemistry, Kazan Scientific Centre, Russian Academy of Sciences, 420083, Kazan

    V. A. Mamedov, E. A. Berdnikov, V. N. Valeeva, I. E. Ismaev, I. Ch. Rizvanov, L. A. Antokhina & I. A. Nuretdinov

  2. V.I.Ulyanov-Lenin Kazan State University, 420008, Kazan

    P. P. Chernov

Authors
  1. V. A. Mamedov
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  2. E. A. Berdnikov
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  3. V. N. Valeeva
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  4. I. E. Ismaev
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  5. I. Ch. Rizvanov
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  6. L. A. Antokhina
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  7. I. A. Nuretdinov
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  8. P. P. Chernov
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1962–1965, November, 1993.

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Mamedov, V.A., Berdnikov, E.A., Valeeva, V.N. et al. Six-membered cyclic semiaminal as intermediate in the synthesis of thiazoles from thiosemicarhazide and α-haloketones. Russ Chem Bull 42, 1879–1882 (1993). https://doi.org/10.1007/BF00699008

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  • DOI: https://doi.org/10.1007/BF00699008

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