Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 544–545 | Cite as

Investigations in the 1,2,4-triazole series

IX. Synthesis of some substituted 1-phenyl-1, 2, 4-triazoles
  • E. G. Kovalev
  • I. Ya. Postovskii


To select a method for the synthesis of the previously difficulty accessible 5-bromo-1-phenyl-1,2,4-triazole (I) and 1-phenyl-1,2,4-triazoline-5-thione (II), a MO LCAO calculation has been carried out in Huckel's approximation of the energies of the radical, electrophilic, and nucleophilic localization on the various carbon atoms of 1-phenyl-1,2,4-triazole (III). In accordance with this calculation, the required compounds have been obtained in good yields by reactions taking place by a radical mechanism: I by bromination with bromosuccinimide and II by the direct thionation of III. The high reactivity of the bromine atom in position 5 has been noted.


Organic Chemistry Carbon Atom Triazole Bromine Good Yield 
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  1. 1.
    I. Ya. Postovskii and I. L. Shegal, KhGS [Chemistry of Heterocyclic Compounds], 2, 443, 1966.Google Scholar
  2. 2.
    B. Pullman and A. Pullman, Quantum Biochemistry [Russian translation], IL, Moscow, p. 92, 1965.Google Scholar
  3. 3.
    B. Pullman, Rev. Mod. Phys., 32, 428, 1960.Google Scholar
  4. 4.
    B. Chubar, Mechanisms of Organic Reactions [Russian translation], IL, Moscow, p. 116, 1963.Google Scholar
  5. 5.
    L. Rolla, Gazz. Chim. Ital., 38, 348, 1908.Google Scholar
  6. 6.
    M. Pesson, S. Dupin, and G. Polmans, Bull. Soc. Chim. France, 1581, 1961.Google Scholar
  7. 7.
    N. V. Koshkin, Tr. Leningr. tekhnol. inst. pishchev. prom., 15, 91, 1958; C. A. 53, 19676, 1959.Google Scholar
  8. 8.
    G. Pellizzari and A. A. Ferro, Gazz. Chim. Ital., 28, 555, 1898.Google Scholar
  9. 9.
    Minoru Sekiya and Shizuma Ishikawa, Yakugaku Zasshi, 78, 549, 1958; C. A., 52, 17244, 1958.Google Scholar
  10. 10.
    L. Rolla, Gazz. Chim. Ital., 38, 343, 1908.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • E. G. Kovalev
    • 1
  • I. Ya. Postovskii
    • 1
  1. 1.Kirov Ural Polytechnical InstituteSverdlovsk

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