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Reactions of Malonothioamide Derivatives with Azides*

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of primary and tertiary malonothioamides with aryl and sulfonyl azides can take place in three directions, depending on the nature of the thioamides and azides. Ethoxycarbonylthioacetamide reacts with aryl azides with the formation of ethyl 5-amino-1-aryl-1,2,3-triazole-4-carboxylates. In reaction with aryl azides tertiary thioamides of cyanoacetic acid form 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides, and in reaction with tosyl azide they form 5-amino-4-carboxamidino-1,2,3-thia-diazoles. Hypothetical mechanisms for the transformations are discussed.

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Authors and Affiliations

  1. Ural Federal University named after the First President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    L. N. Dianova, V. S. Berseneva, O. S. El’tsov & V. A. Bakulev

  2. State Laboratory of Heteroorganic Chemistry, Nankai University, 94 Beijin St., Tianjing, 300071, China

    Z.-J. Fan

Authors
  1. L. N. Dianova
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  2. V. S. Berseneva
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  3. O. S. El’tsov
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  4. Z.-J. Fan
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  5. V. A. Bakulev
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Correspondence to V. A. Bakulev.

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*Dedicated to Academician O. N. Chupakhin on the occasion of his 80th birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1055-1061, July, 2014.

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Dianova, L.N., Berseneva, V.S., El’tsov, O.S. et al. Reactions of Malonothioamide Derivatives with Azides*. Chem Heterocycl Comp 50, 972–978 (2014). https://doi.org/10.1007/s10593-014-1552-x

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  • DOI: https://doi.org/10.1007/s10593-014-1552-x

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