Abstract
Alkylation of tetrazole and its 5-substituted derivatives by 5-tert-butyl, isopropyl, and cyclohexyl alcohols in concentrated H2SO4 results in high yields of the corresponding 2-alkyltetrazoles alone, irrespective of electronic properties and size of the substituent at the 5-position of the tetrazole ring. The tert-butylation of tetrazole in phosphoric acid results in the formation of a mixture of isomeric 1- and 2-substituted derivatives, the concentration of the 1-isomer increasing with decrease in the concentration of the acid in the mixture.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
G. I. Koldobskii, V. A. Ostrovskii, and V. S. Poplavskii, Khim. Geterotsikl. Soedin., No. 10, 1299 (1981).
F. R. Benzon, Heterocyclic Compounds, R. Elderfield (ed.) [Russian translation], Vol. 8, Mir, Moscow (1969), p. 7.
A. V. Sachivko, V. P. Tverdokhlebov, and I. V. Tselinskii, Zh. Org. Khim., 22, 206 (1986).
A. V. Sachivko, V. P. Tverdokhlebov, and I. V. Tselinskii, Zh. Org. Khim., 22, 1112 (1986).
I. Yu. Shirobokov, A. V. Sachivko, V. P. Tverdokhlebov, V. P. Ostrovskii, I. V. Tselinskii, and G. I. Koldobskii, Zh. Org. Khim., 22, 1763 (1986).
A. O. Koren', V. A. Ostrovskii, P. N. Gaponik, I. E. Titova, V. S. Poplavskii, G. V. Avetikyan, and G. I. Koldobskii, Zh. Obshch. Khim., 58, 825 (1988).
R. J. Spear, Austral. J. Chem., 37, 2453 (1984).
R. A. Henry, J. Heterocycl. Chem., 13, 391 (1976).
D. M. Zimmerman and R. A. Olofson, Tetrahedron Lett., 58, 5081 (1969).
H. Quast, L. Bieber, and G. Meichsner, Ann., No. 5, 469 (1987).
P. N. Gaponik, V. P. Karavai, and Yu. V. Grigor'ev, Khim. Geterotsikl. Soedin., No. 11, 1521 (1985).
O. A. Ivashkevich and P. N. Gaponik, Dokl. Akad. Nauk Belorussian SSR, 30, 523 (1986).
V. A. Ostrovskii, G. I. Koldobskii, N. P. Shirokova, and V. S. Poplavskii, Khim. Geterosikl. Soedin., No. 4, 559 (1981).
V. A. Ostrovskii, N. S. Panina, G. I. Koldobskii, B. V. Gidaspov, and I. Yu. Shirobokov, Zh. Org. Khim., 15, 844 (1979).
P. R. Srinivasan and R. L. Lichter, J. Magn. Reson., 28, 227 (1977).
P. N. Gaponik and V. P. Karavai, Vestn. Beloruss. Gos. Un-ta, Ser. 2, No. 3, 51 (1980).
W. G. Finnegan, R. A. Henry, and R. Lofquist, J. Am. Chem. Soc., 80, 3908 (1958).
W. P. Norris, J. Org. Chem., 27, 3248 (1962).
J. H. Nelson, N. E. Takach, R. A. Henry, D. W. Moore, W. M. Tolles, and G. A. Gray, Magn. Reson. Chem., 24, 984 (1986).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1643–1647, December, 1990.
Rights and permissions
About this article
Cite this article
Koren', A.O., Gaponik, P.N. Selective N(2) alkylation of tetrazole and 5-substituted tetrazoles by alcohols. Chem Heterocycl Compd 26, 1366–1370 (1990). https://doi.org/10.1007/BF00473965
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00473965