Abstract
1(2)-Methyl-5-aminotetrazoles and 2-(Β-cyanoethyl)-5-aminotetrazole are nitrated by tetranitromethane in the presence of bases with the formation of salts of the corresponding 5-nitroaminotetrazole derivatives. In contrast to this, decyanoethylation takes place in nitration of 1-(Β-cyanoethyl)-5-aminotetrazole by tetranitromethane with the formation of 5-nitroaminotetrazole salt. The structure of the 2-methyl-5-nitroaminotetrazole salts (using the 2-methyl-5-nitroaminotetrazole potassium salt) was confirmed by x-ray structural analysis.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
A. G. Mayants, K. G. Pyreseva, and S. S. Gordeichuk, Zh. Org. Khim., 22, 2120 (1986).
A. G. Mayants, K. G. Pyreseva, S. S. Gordeichuk, and T. V. Gordeichuk, Zh. Org. Khim., 22, 2124 (1986).
A. G. Mayants, K. G. Pyreseva, and S. S. Gordeichuk, Zh. Org. Khim., 24, 884 (1988).
J. A. Garrison and R. M. Herbst, J. Org. Chem., 22, 278 (1957).
A. G. Mayants, S. S. Gordeichuk, V. A. Shlyapochnikov, T. V. Gordeichuk, and V. P. Gorelik, Khim. Geterosikl. Soedin., No. 11, 1569 (1984).
P. Rochlin, D. B. Murphy, and S. Hell, J. Am. Chem. Soc., 76, 1451 (1954).
A. G. Mayants, N. A. Klinova, and S. S. Gordeichuk, Khim. Geterosikl. Soedin., No. 7, 945 (1987).
E. Laviron, P. Fournazi, and J. Greusard, Bull. Soc. Chim., No. 4, 1255 (1967).
N. Jonathan, J. Mol. Spectrosc., 5, 101 (1960).
V. G. Avakyan, V. A. Chekrygin, and A. N. Kislinskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2687 (1969).
V. G. Avakyan, V. A. Shlyapochnikov, and V. A. Chekrygin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 948 (1972).
V. A. Shlyapochnikov, N. O. Cherskaya, N. S. Morozova, T. N. Ivshina, V. P. Ivshin, and K. I. Bakhtin, Zh. Obshch. Khim., 53, 2334 (1983).
N. O. Cherskaya, V. A. Shlyapochnikov, V. P. Ivshin, and T. N. Ivshina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1533 (1986).
A. G. Mayants, V. V. Erina, and S. S. Gordeichuk, Zh. Org. Khim., 25, 419 (1989).
A. G. Mayants and K. G. Pyreseva, Zh. Org. Khim., 23, 2236 (1987).
E. De Vries and E. S. Gantz, J. Am. Chem. Soc., 76, 1008 (1954).
E. Lieber, S. Patinkin, and H. H. Tao, J. Am. Chem. Soc., 73, 1792 (1951).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1067–1071, August, 1991.
Rights and permissions
About this article
Cite this article
Mayants, A.G., Klimenko, V.S., Erina, V.V. et al. N-nitration of 1(2)-substituted 5-aminotetrazoles with tetranitromethane. Chem Heterocycl Compd 27, 854–858 (1991). https://doi.org/10.1007/BF00472285
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00472285