Synthetic routes towards tetrazolium and triazolium dinitromethylides |
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| Authors: | A R Katritzky G L Sommen A V Gromova R M Witek P J Steel R Damavarapu |
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| Institution: | (1) Center for Heterocyclic Compounds, University of Florida, Department of Chemistry, Gainesville, Florida 32611-7200, USA;(2) Department of Chemistry, University of Canterbury, Christchurch, New Zealand;(3) US Army ARDEC, Picatinny Arsenal, USA |
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| Abstract: | Tetrazolium-5-dinitromethylide sodium salt has been prepared (91%) by cyclization of 1-amino-1-hydrazino-2,2-dinitroethene with nitrous acid in water. 5-Imino-1-(hydroxyiminonitromethyl) derivatives were obtained by nitration of 2-(5-amino-1,3-dimethyl-1H-1,2,4-triazol-4-ium-4-yl)- and 2-(5-amino-4-methyl-1H-tetrazolium-1-yl)acetate complex salts. Treatment of 4-methyl-1-(2-oxopropyl)-1-tetrazolium methylsulfate with nitric and sulfuric acid gave methyl (3-nitro-1,2,4-oxadiazol-5-yl)amine (27%) probably via dinitromethylide followed by cyclization and loss of nitrogen.__________Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 127–134, January, 2005. |
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| Keywords: | nitrolic acid oxadiazole tetrazolium-5-dinitromethylide sodium salt X-Ray structure |
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