Reactions of 3-nitro-1,2,4-triazoles with alkylating agents. 6*. Alkylation of a neutral heterocycle by alcohols in acid media* |
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Authors: | A. G. Sukhanova G. V. Sakovich G. T. Sukhanov |
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Affiliation: | (1) Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biisk, 659322, Russia;(2) Altai Federal State Unitary Enterprise, Federal Research & Production Center, Biisk, 659322, Russia |
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Abstract: | Reaction of 3-nitro-1,2,4-triazole and 5-methyl-3-nitro-1,2,4-triazole with secondary and tertiary alcohols in conc. H2SO4 takes place at the N(2) atom. Alkylation by 2-propanol occurs regioselectively to form the 1-isopropyl-3-nitro-and 1-isopropyl-3-methyl-5-nitro-1,2,4-triazoles. As a consequence of isomerization the alkylation using cyclohexyl or tert-butyl alcohols gives respectively a mixture of regioisomers substituted at atom N(1) (1-cyclohexyl-3-nitro-and 1-cyclohexyl-5-methyl-3-nitro-1,2,4-triazoles) and at atom N(2) (5-nitro-1-cyclohexyl-and 1-cyclohexyl-3-methyl-5-nitro-1,2,4-triazoles) and, in the second case, to 1-tert-butyl-3-nitro-1,2,4-triazole. * For Communication 5 see [1]. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1680–1687, November, 2008. |
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Keywords: | 3-nitro-1,2,4-triazoles alkylation regioselectivity |
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