Synthesis of tetrazole-containing chlorohydrins and epoxides

  • Yuri V. Grigoriev Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus https://orcid.org/0000-0002-8153-835X
  • Yulia M. Yurkova V. A. Belyi Metal-Polymer Research Institute, National Academy of Sciences of Belarus, 32a Kirava Street, 246050 Gomiel, Belarus
  • Inna M. Grigorieva Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus
  • Oleg A. Ivashkevich Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

Abstract

The alkylation of NH-unsubstituted tetrazoles and 1-substituted 5-mercaptotetrazoles with epichlorohydrine followed by dehydrochlorination of the resulting chlorohydrins was found to be a convenient method for the preparation of tetrazole-containing epoxides. Alkylation reaction was shown to proceed with a yield more than 90 %, both in the presence of bases as a catalyst and without the catalytic action of bases using excess of epichlorohydrine. Alkylation with epichlorohydrine in the absence of bases as a catalyst is more preferable in terms of formation of by-products and, as a consequence, purification of target compounds. Tetrazolylepoxides can also be obtained by a two-step process involving hydroxybromination of tetrazole-containing alkenes to form intermediate bromohydrins and subsequent dehydrobromination of latter.

Author Biographies

Yuri V. Grigoriev, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

PhD (chemistry), docent; head of the laboratory for chemistry of condensed systems

Yulia M. Yurkova, V. A. Belyi Metal-Polymer Research Institute, National Academy of Sciences of Belarus, 32a Kirava Street, 246050 Gomiel, Belarus

junior researcher at the department 4 «Friction, lubrication and workability of materials»

Inna M. Grigorieva, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

researcher at the laboratory for chemistry of condensed systems

Oleg A. Ivashkevich, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieningradskaja Street, Minsk 220006, Belarus

doctor of science (chemistry), academician of the National Academy of Sciences of Belarus; chief researcher at the laboratory for chemistry of condensed systems

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Published
2024-08-13
Keywords: tetrazole derivatives, functionalisation, chlorohydrins, epoxides, synthesis
Supporting Agencies The research was supported by the Ministry of Education of the Republic of Belarus (project «Development of effective methods for the synthesis of tetrazole-containing epoxides promising for use in energy-intensive condensed systems», state registration No. 20231505).
How to Cite
Grigoriev, Y. V., Yurkova, Y. M., Grigorieva, I. M., & Ivashkevich, O. A. (2024). Synthesis of tetrazole-containing chlorohydrins and epoxides. Journal of the Belarusian State University. Chemistry, 2, 36-45. Retrieved from https://journals.bsu.by/index.php/chemistry/article/view/6470
Issue
No 2 (2024): Journal of the Belarusian State University. Chemistry
Section
Original Articles

Copyright (c) 2024 Journal of the Belarusian State University. Chemistry

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