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.
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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.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya. No. 3, pp. 480–484, March, 2000.
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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
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DOI: https://doi.org/10.1007/BF02494779