Chemistry of Heterocyclic Compounds

, Volume 47, Issue 1, pp 55–59 | Cite as

Reactions of 3-nitro-1,2,4-triazole derivatives with alkylating agents. 8*. Alkylation of 3-nitro-5-R-1,2,4-triazoles with derivatives of diethylene glycol in the presence of alkali

  • G. T. SukhanovEmail author
  • G. V. Sakovich
  • A. G. Sukhanova
  • J. V. Filippova
  • J. Yu. Oleshchenko

The interaction of 3-nitro-1,2,4-triazole and 5-methyl-3-nitro-1,2,4-triazole with bifunctional agents ‒ β,β′-dichloro- and β,β′-(dinitroxy)diethyl ethers ‒ in the presence of alkali proceeds with the formation of a mixture of products substituted at the N(1) and N(2) atoms of the heterocycle, consisting of three reaction products, the N(1),N′(1)-, N(1),N′(2)-, and N(2),N′(2) isomeric derivatives of nitrotriazoles. Replacement of the Cl leaving group in the alkylating agent by a NO2 group does not lead to a substantial change in the degree of conversion and overall yield of alkylation products. The ratio of N(1),N′(1):N(1),N′(2):N(2),N′(2) isomeric reaction products from 3-nitro-1,2,4-triazole was (82.0-85.7): (7.7-9.9):(6.6-8.1), and from 5-methyl-3-nitro-1,2,4-triazole was (76.9-79.8):(10.1:11.4):(10.1-11.7) respectively.


3-nitro-5-R-1,2,4-triazoles diethylene glycol derivatives alkylation selectivity 


  1. 1.
    A. G. Sukhanova, G. V. Sakovich, and G. T. Sukhanov, Khim. Geterotsikl. Soedin., 603 (2010). [Chem. Heterocycl. Comp., 46, 478 (2010)].Google Scholar
  2. 2.
    A. N. Terpigorev, M. B. Shcherbinin, A. G. Bazanov, and I. V. Tselinskii, Zh. Org. Khim., 18, 463 (1982).Google Scholar
  3. 3.
    T. P. Kofman and G. Yu. Kartseva, Zh. Org. Khim., 37, 707 (2001).Google Scholar
  4. 4.
    V. V. Semenov, B. I. Ugrak, S. A. Shevelev, M. I. Kanishchev, A. T. Barshnikov, and A. A. Fainzil’berg, Izv. Akad. Nauk SSSR. Ser. Khim., 1827 (1990).Google Scholar
  5. 5.
    M. P. Hay, H. H. Lee, W. R. Wilson, P. B. Roberts, and W. A. Denny, J. Med. Chem., 38, 1928 (1995).CrossRefGoogle Scholar
  6. 6.
    L. I. Bagal, M. S. Pevzner, N. I. Sheludyakova, and V. M. Kerusov, Khim. Geterotsikl. Soedin., 265 (1970). [Chem. Heterocycl. Comp., 6, 245 (1970)].Google Scholar
  7. 7.
    A. P. Kruglik, S. M. Leshchev, E. M. Rakhman’ko, O. N. Bubel’, and G. V. Asratyan, Zh. Prikl. Khim., 64, 1721 (1991).Google Scholar
  8. 8.
    R. W. Middleton, H. Monney, and J. Parrick, Synthesis, 740 (1984).Google Scholar
  9. 9.
    G. T. Sukhanov and A. Yu. Lukin, Khim. Geterotsikl. Soedin., 1020 (2005). [Chem. Heterocycl. Comp., 41, 861 (2005)].Google Scholar
  10. 10.
    G. T. Sukhanov, A. G. Sukhanova, and A. Yu. Lukin, Khim. Geterotsikl. Soedin., 1168 (2005). [Chem. Heterocycl. Comp., 41, 994 (2005)].Google Scholar
  11. 11.
    G. T. Sukhanov, A. G. Sukhanova, and Yu. V. Il’yasova, Khim. Geterotsikl. Soedin., 1378 (2006). [Chem. Heterocycl. Comp., 42, 1197 (2006)].Google Scholar
  12. 12.
    G. T. Sukhanov, G. V. Sakovich, and A. G. Sukhanova, Khim. Geterotsikl. Soedin., 1680 (2008). [Chem. Heterocycl. Comp., 44, 1368 (2008)].Google Scholar
  13. 13.
    G. T. Sukhanov, K. K. Bosov, A. G. Sukhanova, and P. I. Kalmykov, Vestn. KGTU, Spets. Vyp., 93 (2008).Google Scholar
  14. 14.
    G. T. Sukhanov, A. G. Sukhanova, and Yu. V. Sheikov, Khim. Geterotsikl. Soedin., 927 (2007). [Chem. Heterocycl. Comp., 43, 786 (2007)].Google Scholar
  15. 15.
    L. I. Bagal, M. S. Pevzner, A. N. Frolov, and N. I. Sheludyakova, Khim. Geterotsikl. Soedin., 259 (1970). [Chem. Heterocycl. Comp., 6, 240 (1970)].Google Scholar
  16. 16.
    V. V. Mel'nikov, V. V. Stolpakova, M. S. Pevzner, and B. V. Gidaspov, Khim. Geterotsikl. Soedin., 707 (1973). [Chem. Heterocycl. Comp., 9, 651 (1973)].Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • G. T. Sukhanov
    • 1
    Email author
  • G. V. Sakovich
    • 1
  • A. G. Sukhanova
    • 1
  • J. V. Filippova
    • 1
  • J. Yu. Oleshchenko
    • 1
  1. 1.Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of SciencesBiyskRussia

Personalised recommendations