THIAZOLIDINE-2,4-DIONE IN BENZOYLATION REACTION

Authors

  • Igor B. Levshin N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977
  • Nina A. Rastorgeva N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977
  • Alexey V. Kiselev N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977
  • Alexandr S. Vedenkin N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977
  • Sergey V. Stovbun N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977
  • Andrey V. Churakov Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Ave., Moscow 119991
  • Oleg Yu. Saveliev Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University, 27/1 Lomonosovsky Ave., Moscow 119991
  • Vladimir I. Polshakov Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University, 27/1 Lomonosovsky Ave., Moscow 119991

DOI:

https://doi.org/10.1007/4868

Keywords:

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

Abstract

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.

Author Biographies

Igor B. Levshin, N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977

Senior researcher of the  laboratory of Chemical Physics of Biosystems. Prof.

Nina A. Rastorgeva, N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977

Researcher of the  laboratory of Chemical Physics of Biosystems. Ph.D.

Alexey V. Kiselev, N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977

Researcher of the  laboratory of Chemical Physics of Biosystems. Ph.D.

Alexandr S. Vedenkin, N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977

Researcher of the  laboratory of Chemical Physics of Biosystems.

Sergey V. Stovbun, N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow 117977

Head of the  laboratory of Chemical Physics of Biosystems. Prof.

Andrey V. Churakov, Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Ave., Moscow 119991

Senior researcher of Laboratory of crystal chemistry and X-ray analysis. Ph.D

Oleg Yu. Saveliev, Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University, 27/1 Lomonosovsky Ave., Moscow 119991

Researcher of the  Center for Magnetic Tomography & Spectroscopy

Vladimir I. Polshakov, Faculty of Fundamental Medicine, M. V. Lomonosov Moscow State University, 27/1 Lomonosovsky Ave., Moscow 119991

Sinior researcher of the  Center for Magnetic Tomography & Spectroscopy. Prof.

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Published

2019-03-11

Issue

Vol. 55 No. 2 (2019)

Section

Original Papers