Synthesis and properties of carbazolyl- and phenothiazinyl-bis-tetrazoles

  • Yuri V. Grigoriev Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus https://orcid.org/0000-0002-8153-835X
  • Igor A. Sadovsky Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus
  • Chen Bowen Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus
  • Inna M. Grigorieva Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus
  • Oleg A. Ivashkevich Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus
DOI: https://doi.org/10.33581/2520-257X-2023-1-20-27

Abstract

The possibility of introducing tetrazolyl groups into carbazole and phenothiazine molecules by substitution of hydrogen atoms of carbocycles has been investigated. It has been shown that the classical nitration-reduction methods can be used for preparation of 3,6-diaminocarbazole and 3,7-diaminophenothiazine which can be involved into reaction with triethyl orthoformate and sodium azide, giving in moderate yield 3,6-di(tetrazol-1-yl)carbazole and 3,7-di(tetrazol-1- yl)phenothiazine, respectively. The composition and structure of the obtained compounds were determined by elemental analysis, NMR and IR spectroscopy. The introduction of tetrazolyl groups into the carbazole and phenothiazine molecules shifts their maximum absorption in UV-VIS spectra into the short-wave region by 85 nm in the case of phenothiazine and by 15 nm in the case of carbazole. The latter is due to electron acceptor influence of tetrazole cycles and, as a consequence, redistribution of π-electron density in carbazolyl- and phenothiazinyl-bis-tetrazoles molecules as compared to the original carbazole and phenothiazine. It was found that 3,7-di(tetrazol-1-yl)phenothiazine is an acid-base indicator, whose aqueous solutions change colour in the pH range of 11.6–10.5.

Author Biographies

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

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

Igor A. Sadovsky, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus

master’s degree student at the department of inorganic chemistry, faculty of chemistry

Chen Bowen, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus

master’s degree student at the department of inorganic chemistry, faculty of chemistry

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

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

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Published
2023-03-03
Keywords: carbazole, phenothiazine, functionalisation, 1-substituted tetrazoles, synthesis
Supporting Agencies The research was supported by the Ministry of Education of the Republic of Belarus (assignment 2.1.01.01 of the state program of scientific research «Chemical processes, reagents and technologies, bioregulators and bioorgchemistry».
How to Cite
Grigoriev, Y. V., Sadovsky, I. A., Bowen, C., Grigorieva, I. M., & Ivashkevich, O. A. (2023). Synthesis and properties of carbazolyl- and phenothiazinyl-bis-tetrazoles. Journal of the Belarusian State University. Chemistry, 1, 20-27. https://doi.org/10.33581/2520-257X-2023-1-20-27
Issue
No 1 (2023): Journal of the Belarusian State University. Chemistry
Section
Original Articles

Copyright (c) 2023 Journal of the Belarusian State University. Chemistry

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