Structural Chemistry

, Volume 23, Issue 5, pp 1441–1448

Does dehydrocyclization of 4-benzoylthiosemicarbazides in acetic acid lead to s-triazoles or thiadiazoles?

  • Agata Siwek
  • Paweł Stączek
  • Urszula Kosikowska
  • Anna Malm
  • Piotr Paneth
  • Stefan Jankowski
Original Research

Abstract

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.

Keywords

Thiadiazole Triazole NMR DFT 

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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Agata Siwek
    • 1
  • Paweł Stączek
    • 2
  • Urszula Kosikowska
    • 3
  • Anna Malm
    • 3
  • Piotr Paneth
    • 4
  • Stefan Jankowski
    • 5
  1. 1.Department of Organic Chemistry, Faculty of PharmacyMedical UniversityLublinPoland
  2. 2.Department of Genetics of MicroorganismsUniversity of LodzLodzPoland
  3. 3.Department of Pharmaceutical Microbiology, Faculty of PharmacyMedical UniversityLublinPoland
  4. 4.Institute of Applied Radiation ChemistryTechnical University of LodzLodzPoland
  5. 5.Institute of Organic ChemistryTechnical University of LodzLodzPoland

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