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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. Sukhanov
  • G. V. Sakovich
  • A. G. Sukhanova
  • J. V. Filippova
  • J. Yu. Oleshchenko
Article

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.

Keywords

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

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • G. T. Sukhanov
    • 1
  • 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

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