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Reactions of N-sulfonyl-1,2,3-thiadiazole-4-carbimidamides with sulfonyl chlorides: regiospecific synthesis and structure of 2-sulfonyl-1,2,3-triazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Sulfonylation of 1,2,3-thiadiazolecarboxylic acid amidines in the presence of a base was found to be accompanied by the Cornforth rearrangement of the 1,2,3-thiadiazole ring into 1,2,3-triazole leading to the formation of 2-substituted 1,2,3-triazoles in high yields.

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This work was supported by the Russian Foundation for Basic Research (grant 18-03-00715).

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Authors and Affiliations

  1. Department of Technology of Organic Synthesis, Ural Federal University named after the first Prezident of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Tetyana V. Beryozkina, Valeriy O. Filimonov, Lidiya N. Dianova, Tatiana А. Pospelova & Vasiliy А. Bakulev

  2. Department of Organic and Biomolecular Chemistry, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Pavel А. Slepukhin

  3. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St., Yekaterinburg, 620990, Russia

    Pavel А. Slepukhin & Vasiliy А. Bakulev

  4. Department of Organic Chemistry, Lomonosov Moscow State University, 1 Build. 3 Leninskie Gory, Moscow, 119992, Russia

    Dmitriy M. Mazur

Authors
  1. Tetyana V. Beryozkina
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  2. Valeriy O. Filimonov
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  3. Lidiya N. Dianova
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  4. Pavel А. Slepukhin
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  5. Dmitriy M. Mazur
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  6. Tatiana А. Pospelova
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  7. Vasiliy А. Bakulev
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Correspondence to Vasiliy А. Bakulev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(6), 547–553

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Beryozkina, T.V., Filimonov, V.O., Dianova, L.N. et al. Reactions of N-sulfonyl-1,2,3-thiadiazole-4-carbimidamides with sulfonyl chlorides: regiospecific synthesis and structure of 2-sulfonyl-1,2,3-triazoles. Chem Heterocycl Comp 55, 547–553 (2019). https://doi.org/10.1007/s10593-019-02494-6

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