Abstract
Ketones of the 3-nitro-5-R-1,2,4-triazole series react with hydrazoic acid in concentrated sulfuric acid to give triazolyl-substituted acetamides. Acid hydrolysis of the latter leads to 1-aminoalkyl-3-nitro-5-R-1,2,4-triazoles. Intramolecular cyclization with the elimination of HNO2 and the formation of 2-nitro-5,6-dihydro-1H-imidazo[2,3-b]-1,2,4-triazole was noted in the case of 1-(2′-aminoethyl)-3,5-dinitro-1,2,4-triazole.
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T. P. Kofman, T. L. Uspenskaya, N. Yu. Medvedeva, and M. S. Pevzner, Khim. Geterotsikl. Soedin., No. 7, 991 (1976).
G. I. Koldobskii, G. F. Tereshchenko, and L. I. Bagal, Zh. Org. Khim., 6, 2395 (1970).
T. P. Kofman, V. I. Manuilova, M. S. Pevzner, and T. N. Timofeeva, Khim. Geterotsikl. Soedin., No. 5, 705 (1975).
L. I. Bagal, M. S. Pevzner, and V. Ya. Samarenko, Khim. Geterotsikl. Soedin., No. 2, 269 (1970).
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See [1] for communication XX.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1271–1273, September, 1977.
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Kofman, T.P., Medvedeva, N.Y., Uspenskaya, T.L. et al. Heterocyclic nitro compounds. Chem Heterocycl Compd 13, 1026–1029 (1977). https://doi.org/10.1007/BF00472466
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DOI: https://doi.org/10.1007/BF00472466