Triethyl orthobenzoate in reactions with primary amines and sodium azide

Authors

  • 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
  • Evgeny Y. Grigoriev Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus
  • Ludmila S. Ivashkevich 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

Keywords:

triethyl orthobenzoate, primary amines, N-substituted benzamides, benzamidines, 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 programme of scientific research «Chemical processes, reagents and technologies, bioregulators and bioorgchemistry»).

Abstract

The reaction of triethyl orthobenzoate with primary amines and sodium azide has been studied. It has been established that, in contrast to the orthoesters of formic, acetic and monochloroacetic acids, whose heterocyclisation with primary amines and sodium azide leads to the formation of 1- and 1,5-substituted tetrazoles, triethyl orthobenzoate does not form corresponding 1-substituted 5-phenyltetrazoles under analogous conditions. The main reaction products are N-substituted benzamides. When ethylenediamine or diethylenetriamine is used as primary amine, the main reaction products are hydrolysis-resistant cyclic amidines, namely 2-phenyl-4,5-dihydroimidazole and N-(2-(2-phenyl-4,5-dihydroimidazol-1-yl)ethyl)benzamide, respectively. The obtained data indicate that the azide ion does participate in the reaction under study.

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

  • Evgeny Y. Grigoriev, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus

    junior researcher at the laboratory for chemistry of condensed systems

  • Ludmila S. Ivashkevich, Research Institute for Physical Chemical Problems, Belarusian State University, 14 Lieninhradskaja Street, Minsk 220006, Belarus

    PhD (chemistry), docent; head of the laboratory of physico-chemical investigations

  • 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

Issue

No. 1 (2023): Journal of the Belarusian State University. Chemistry

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How to Cite

[1]
Grigoriev, .Y.V. et al. 2023. Triethyl orthobenzoate in reactions with primary amines and sodium azide. Journal of the Belarusian State University. Chemistry. 1 (Mar. 2023), 50–57. DOI:https://doi.org/10.33581/2520-257X-2023-1-50-57.