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
DOI:
https://doi.org/10.1007/2175Keywords:
3-nitro-5-R-1, 2, 4-triazoles, diethylene glycol derivatives, alkylation, selectivityAbstract
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.
How to Cite
Sukhanov, G. T.; Sakovich, G. V.; Sukhanova, A. G.; Filippova, J. V.; Oleshchenko, J. Yu. Chem. Heterocycl. Compd. 2011, 47(1), 55. [Khim. Geterotsikl. Soedin. 2011, 75.]
