GEM-DINITRO COMPOUNDS IN ORGANIC SYNTHESIS. 3. SYNTHESES OF 4-NITRO-1,2,3-TRIAZOLES FROM GEM-DINITRO COMPOUNDS

Article abstract of DOI:10.1007/BF01150904

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-(β,β-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.Keywords: gem-dinitro compounds, 4-nitro-1,2,3-triazoles, gem-dinitroethylenes, dinitroacetic acid ester, N-(β,β-dinitroethyl)-N,N-dialkylamines, 2,2-dinitroethanol acetate, 1,1,1-trinitroalkanes, nitration, cyclization, 2,4-dinitro-1,2,3-triazole.