Abstract
A new approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides involves the treatment ofN-nitroanilines containing anortho-(tert-butyl-NNO-azoxy) group with phosphoric anhydride or phosphorus pentachloride. The reaction is supposed to proceed through an intermediate diazonium oxide cation.
Similar content being viewed by others
References
A. M. Churakov, S. L. Ioffe, Yu. A. Strelenko, and V. A. Tartakovsky,Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 718 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990,39, 639 (Engl. Transl.)].
(a) A. M. Churakov, S. L. Ioffe, and V. A. Tartakovsky,Mendeleev Commun., 1991, 101;
(b)Ibid. A. M. Churakov, S. L. Ioffe, and V. A. Tartakovsky,Mendeleev Commun., 1995, 227.
A. M. Churakov, S. L. Ioffe, V. A. Tartakovsky, O. G. Busygina, Yu. V. Khropov, and I. S. Severina, RF Patent 2, 123, 526, 1998.
W. M. Weaver, inThe Chemistry of the Nitro and Nitroso Groups, Ed. H. Feuer. Wiley Interscience, New York, 1970,2. ch. 1.
E. Kolehmainen, K. Laihia, R. Kauppinen, R. Gawinecki, and D. Rasala,Magn. Reson. Chem., 1993,31, 659.
A. M. Churakov, O. Yu. Smirnov, S. L. Ioffe, Yu. A. Strelenko, and V. A. Tartakovsky,Izv. Akad. Nauk, Ser. Khim., 1994, 1620 [Russ. Chem. Bull., 1994,43, 1532 (Engl. Transl.)].
R. C. Zawalski and P. Kovacic,J. Org. Chem., 1979,44, 2130.
G. F. Wright, inThe Chemistry of the Nitro and Nitroso Groups, Ed. H. Feuer, Wiley Interscience. New York, 1969,1, ch. 9.
A. Maquestiau, Y. Van Haverbeke, and R. Flammang,Org. Mass Spectrom., 1973,7, 1267.
D. W. S. Latham, O. Meth-Cohn, and H. Suschitzky,J. Chem. Soc., Perkin Trans. 1, 1977,5, 478.
L. Stefaniak,Org. Magn. Res., 1978,11, 385.
A. M. Churakov, O. Yu. Smirnov, Yu. A. Strelenko, S. L. Ioffe, V. A. Tartakovsky, Yu. T. Struchkov, F. M. Dolgushin, and A. I. Yanovsky,Mendeleev Commun., 1994, 122.
D. F. Ewing,Org. Magn. Reson., 1979,12, 499.
W. Gottardi,Monatsh. Chem., 1973,104, 1681.
N. S. Gruenhut, M. Goldfrank, M. L. Cushing, and G. V. Caesar,Inorganic Synthesis, 1950,3, 78.
F. B. Mallory, K. E. Schueller, and C. S. Wood,J. Org. Chem., 1961,26, 3312.
USSR Inventor's Certificate No. 574, 445,Chem. Abstr., 1978,88, 6895j.
J. M. Prokipcak and P. A. Forte,Can. J. Chem., 1970,48, 3059.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya. No. 3, pp. 480–484, March, 2000.
Rights and permissions
About this article
Cite this article
Frumkin, A.E., Churakov, A.M., Strelenko, Y.A. et al. New approach to the synthesis of benzo[e][1,2,3,4]tetrazine 1,3-dioxides. Russ Chem Bull 49, 482–486 (2000). https://doi.org/10.1007/BF02494779
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02494779