Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.) p. 751 - 757 (1992)
Update date:2022-08-17
Topics:
Baryshnikov, A. T.
Erashko, V. I.
Zubanova, N. I.
Ugrak, B. I.
Shevelev, S. A.
et al.
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.
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