Gem-dinitro compounds in organic synthesis. 3. Syntheses of 4-nitro-1,2,3-triazoles from gem-dinitro compounds

Several chemoselective syntheses have been developed for 4-nitro-1,2,3-triazoles from sodium azide and gem-dinitroethylenes prepared from readily available transformation products of dinitroacetic acid ester: N-(,-dinitroethyl)-N,N-dialkylamines, 2,2-dinitroethanol acetate, a mixture of dinitroacetic acid ester with aliphatic aldehydes, or 1,1,1-trinitroalkanes. Hitherto-unknown 4-nitro-5-amino- and 4,5-dinitro-1,2,3-triazoles have been synthesized via successive transformations of the CH₃ groups in 5-nitro-4-methyltriazole. Nitration of 4-nitro-1,2,3-triazole with nitronium fluoroborate or acetyl nitrate gave an unknown 2,4-dinitro-1,2,3-triazole.N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 4, pp. 958–966, April, 1992.