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Reaction of 2-methyl-3-ethoxycarbonyl-4-hydroxythiophene with hydrazines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Methyl-3-ethoxycarbonyl-4-(N,N-dimethylhydrazino)thiophene (II) and 2-methyl-3-ethoxy-carbonyl-4-(N-phenylhydrazino)thiophene (III) are formed by the action of substituted hydrazines — N,N-dimethylhydrazine and phenylhydrazine — on 2-methyl-3-ethoxycarbonyl-4-hydroxythiophene (I). At the same time, the thiophene ring of hydroxythiophene I undergoes hydrazinolysis under the influence of hydrazine hydrate to form 3-mercaptomethyl-4-ethoxycarbonyl-5-methylpyrazole (IV). Structure IV was proved by IR, UV, and PMR spectroscopy and by hydrogenolysis of IV to the known 3,5-dimethyl-4-ethoxycarbonylpyrazole (V).

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical Chemistry Institute, Moscow

    V. I. Shvedov, V. K. Vasil'eva, A. N. Grinev & N. P. Kostyuchenko

Authors
  1. V. I. Shvedov
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  2. V. K. Vasil'eva
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  3. A. N. Grinev
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  4. N. P. Kostyuchenko
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 759–761, June, 1971.

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Shvedov, V.I., Vasil'eva, V.K., Grinev, A.N. et al. Reaction of 2-methyl-3-ethoxycarbonyl-4-hydroxythiophene with hydrazines. Chem Heterocycl Compd 7, 707–709 (1971). https://doi.org/10.1007/BF00476812

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  • DOI: https://doi.org/10.1007/BF00476812

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