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Ring-chain tautomerism of substituted hydrazones

13. Mercaptoalkylation of hydrazones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of thiiranes with hydrozones leads primarily to 2-mercaptoalkylhydrazones that are capable of undergoing reversible isomerization to the corresponding perhydro-1,3,4-thiadiazines or (in the case of unsubstituted aldohydrazones) to 3-aminothiazolidines. The reaction mixtures, which contain products of side and secondary reactions, were analyzed by Chromatographic mass spectrometry. It is shown that the principal products of mercaptoethylation and mercaptopropylation of acetone hydrazone exists in the form of tautomeric mixtures of chain and ring forms and that the introduction of a methyl substituent in the 6 position of the ring leads to a shift of the equilibrium to favor the perhydro-1,3,4-thiadiazine.

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Authors and Affiliations

  1. A. A. Zhdanov Leningrad State University, 199164, Leningrad

    S. M. Shevchenko & A. A. Potekhin

Authors
  1. S. M. Shevchenko
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  2. A. A. Potekhin
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Additional information

See [1] for our preliminary communication; see [2] for communication 12.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1637–1647, December, 1979.

Original article submitted June 27, 1979.

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Shevchenko, S.M., Potekhin, A.A. Ring-chain tautomerism of substituted hydrazones. Chem Heterocycl Compd 15, 1314–1323 (1979). https://doi.org/10.1007/BF00514734

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  • DOI: https://doi.org/10.1007/BF00514734

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