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首页> 外文期刊>Structural Chemistry >Does dehydrocyclization of 4-benzoylthiosemicarbazides in acetic acid lead to s-triazoles or thiadiazoles?
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Does dehydrocyclization of 4-benzoylthiosemicarbazides in acetic acid lead to s-triazoles or thiadiazoles?

机译：4-乙酸苯甲硫基氨基脲在乙酸中的脱氢环化反应会导致S-三唑或噻二唑吗？

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摘要

Ever since the recognition of strong pharmaceutical activities of triazoles and thiadiazoles, these scaffolds have been the subject of vigorous studies. One of the best strategies for synthesis of these azoles is dehydrocyclization of 1,4-disubstituted thiosemicarbazides, which leads to s-triazoles in alkaline media, whereas in strong acidic media 1,3,4-thiadiazoles are formed. However, the literature is riddled with contradictory communications regarding the nature of the products of such reactions under mild acidic conditions. As these compounds are not amenable to X-ray analysis, we have resorted to NMR and theoretical modelling to resolve this discrepancy. In this article, we present arguments indicating that dehydrocyclization of 4-benzoylthiosemicarbazides in glacial acetic acid leads to thiadiazole derivatives. These structural findings are augmented by studies of bioactivity of a few members of the studied class of compounds.
机译：自从认识到三唑和噻二唑具有很强的药物活性以来，这些支架就成为了研究的主题。合成这些唑的最佳策略之一是1,4-二取代的硫代氨基脲的脱氢环化反应，这会在碱性介质中生成s-三唑，而在强酸性介质中会生成1,3,4-噻二唑。然而，关于在温和的酸性条件下此类反应的产物的性质的文献充斥着矛盾的信息。由于这些化合物不适用于X射线分析，因此我们采用NMR和理论模型来解决这一差异。在本文中，我们提出了一些论据，表明在冰醋酸中4-苯甲酰硫基氨基脲的脱氢环化反应会生成噻二唑衍生物。通过对所研究化合物类别的少数成员的生物活性进行研究，可以增强这些结构发现。

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  • 来源
    《Structural Chemistry》 |2012年第5期|p.1441-1448|共8页
  • 作者

    Agata Siwek; Paweł Stączek; Urszula Kosikowska; Anna Malm; Piotr Paneth; Stefan Jankowski;

  • 作者单位

    Department of Organic Chemistry, Faculty of Pharmacy, Medical University, Chodzki 4a, 20-093, Lublin, Poland;

    Department of Genetics of Microorganisms, University of Lodz, Banacha 12/16, 90-237, Lodz, Poland;

    Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Medical University, Chodzki 1, 20-093, Lublin, Poland;

    Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Medical University, Chodzki 1, 20-093, Lublin, Poland;

    Institute of Applied Radiation Chemistry, Technical University of Lodz, Zeromskiego 116, 90-924, Lodz, Poland;

    Institute of Organic Chemistry, Technical University of Lodz, Zeromskiego 116, 90-924, Lodz, Poland;

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  • 正文语种 eng
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  • 关键词

    Thiadiazole; Triazole; NMR; DFT;

    机译：噻二唑;三唑;NMR;DFT;

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