Abstract
Thermolysis of o-diazidobenzotetrazine 1,3-dioxides was accompanied by cleavage of the C-C bond of the benzene ring to give nonannulated 1,2,3,4-tetrazine 1,3-dioxides. The structures of these first representatives of nonfused 1,2,3,4-tetrazines were confirmed by 13C and 14N NMR spectroscopy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
D. Hurst, in Comprehensive Heterocyclic Chemistry II, Eds A. R. Katritzky, C. W. Rees, and E. F. V. Scriven, Pergamon, Oxford, 1996, 6, Ch. 6.22, 957.
A. M. Churakov and V. A. Tartakovsky, Chem. Rev., 2004, 104, 2601.
V. A. Tartakovsky, I. E. Filatov, A. M. Churakov, S. L. Ioffe, Yu. A. Strelenko, V. S. Kuz’min, G. L. Rusinov, and K. I. Pashkevich, Izv. Akad. Nauk, Ser. Khim., 2004, 2472 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2577].
T. Kaihoh, T. Itoh, K. Yamaguchi, and A. Ohsawa, J. Chem. Soc., Perkin Trans. 1, 1991, 2045.
J. H. Hall and E. Patterson, J. Am. Chem. Soc., 1967, 89, 5856.
S. Marburg and P. A. Grieco, Tetrahedron Lett., 1966, 1305.
K. Banert, Angew. Chem., 1987, 99, 932.
O. Yu. Smirnov, A. Yu. Tyurin, A. M. Churakov, Yu. A. Strelenko, and V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2006, 133 [Russ. Chem. Bull., Int. Ed., 2006, 55, 137].
J. Nakayama, T. Segiri, R. Ohya, and N. Hoshimo, J. Chem. Soc., Chem. Commun., 1980, 791.
S.-J. Chang, Synth. Commun., 1982, 12, 673.
H. Meier, Synthesis, 1972, 5, 235.
T. Nakazawa, M. Kodama, S. Kiroshita, and I. Murata, Tetrahedron Lett., 1985, 26, 335.
D. N. Laikov and Yu. A. Ustynyuk, Izv. Akad. Nauk, Ser. Khim., 2005, 804 [Russ. Chem. Bull., Int. Ed., 2005, 54, 820].
R. Furttero, B. Ferrarotti, A. Serafino, and A. Gasco, Liebigs Ann. Chem., 1990, 335.
L. I. Khmel’nitskii, S. S. Novikov, and T. I. Godovikova, Khimiya furoksanov. Stroenie i sintez [The Chemistry of Furoxanes. Structures and Synthesis], 2nd ed., Nauka, 1996, p. 53 (in Russian).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1589–1594, September, 2006.
Rights and permissions
About this article
Cite this article
Tyurin, A.Y., Churakov, A.M., Strelenko, Y.A. et al. Synthesis of first nonannulated 1,2,3,4-tetrazine 1,3-dioxides. Russ Chem Bull 55, 1648–1653 (2006). https://doi.org/10.1007/s11172-006-0468-8
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0468-8