Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in strongly acidic media |
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Authors: | G V Sakovich G T Sukhanov Yu V Filippova A G Sukhanova K K Bosov |
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Institution: | 1. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, 1 ul. Sotsialisticheskaya, 659322, Biysk, Altai Krai, Russian Federation
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Abstract: | Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in concentrated H2SO4 occurs at all three endocyclic N atoms, giving a mixture of isomeric N(1)-, N(2)-, and N(3)-alkyl-4-nitro-1,2,3-triazoles (alkyl is isopropyl, sec-butyl, and cyclohexyl). The selectivity of the alkylation depends on the alcohol used. The most selective alkylation is provided at the N(2) atom when isopropyl (81%) and sec-butyl alcohols are used (67%). With an increase in the reaction time, also in the order isopropyl-, sec-butyl-, and cyclohexyl-4-nitro-1,2,3-triazoles, the N(2)-isomers undergo isomerization into N(1)-alkyl-4-nitro-1,2,3-triazoles. In all the cases, the fraction of the N(3)-substitution products in the mixtures is 6–30%. |
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