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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 2, pp 178–183 | Cite as

Thiazolidine-2,4-dione in benzoylation reaction

  • Igor B. LevshinEmail author
  • Nina A. Rastorgueva
  • Alexey V. Kiselev
  • Alexandr S. Vedenkin
  • Sergey V. Stovbun
  • Andrei V. Churakov
  • Oleg Yu. Saveliev
  • Vladimir I. Polshakov
Article
  • 42 Downloads

The direction of the benzoylation reaction of thiazolidine-2,4-dione under the conditions of basic and general acid catalysis was studied. It was shown that the direction of benzoylation of thiazolidine-2,4-dione at the cyclic nitrogen atom or oxygen atoms depends on two major factors: the solvent and the presence of cations. A nonpolar solvent and triethylamine direct the reaction toward the formation of the dibenzoyl product, which was isolated and characterized for the first time. The structure of this compound has been unambiguously identified using NMR and X-ray diffraction analysis. A hydrogen bond between the nitrogen atom of the dibenzoyl product and the proton of the chloroform molecule was found in crystal structure.

Keywords

thiazolidine-2,4-dione benzoylation C–H hydrogen bonds 

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Igor B. Levshin
    • 1
    Email author
  • Nina A. Rastorgueva
    • 1
  • Alexey V. Kiselev
    • 1
  • Alexandr S. Vedenkin
    • 1
  • Sergey V. Stovbun
    • 1
  • Andrei V. Churakov
    • 2
  • Oleg Yu. Saveliev
    • 3
  • Vladimir I. Polshakov
    • 3
  1. 1.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussia
  2. 2.Kurnakov Institute of General and Inorganic ChemistryRussian Academy of SciencesMoscowRussia
  3. 3.Faculty of Fundamental MedicineM. V. Lomonosov Moscow State UniversityMoscowRussia

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