Abstract
A new method for the synthesis of benzotetrazine-1,3-dioxides was developed, which involves the reaction of 2-(tert-butyl-NNO-azoxy)-N-nitroanilines with the Ac2O/H2SO4 system. This method was also used for the synthesis of [1,2,5]oxadiazolo[3,4-c]cinnoline-5-oxide from 3-nitramino-4-phenylfurazan. The suggested mechanism of these reactions involves the formation of the intermediate oxodiazonium ion, resulting from acetylation of the oxygen atom of the nitramine group, followed by protonation and ionic dissociation. Then the oxodiazonium ion enters the intramolecular reaction with the neighboring tert-butyl-NNO-azoxy or phenyl group to form the corresponding heterocyclic systems.
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M. S. Klenov, M. O. Ratnikov, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2011, 523 [Russ. Chem. Bull., Int. Ed., 2011, 60, 536].
A. M. Churakov, S. L. Ioffe, V. A. Tartakovsky, Mendeleev Commun., 1991, 101.
A. M. Churakov, O. Yu. Smirnov, S. L. Ioffe, Yu. A. Strelenko, V. A. Tartakovsky, Eur. J. Org. Chem., 2002, 2342.
A. E. Frumkin, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 2000, 480 [Russ. Chem. Bull., Int. Ed., 2000, 49, 482].
V. P. Zelenov, A. A. Lobanova, S. V. Sysolyatin, Mater. dokl. Mezhdunar. nauchno-tekhn. i metodich. konf. “Sovremennye problemy tekhnicheskoi khimii” [Proceedings of the International Scientific Technical and Methodical Conference “Modern Problems of Technical Chemistry”] (Kazan, December 22–24, 2004), Kazan, 2004, 337 (in Russian).
O. Stillich, Chem. Ber., 1905, 38, 1245.
A. M. Churakov, O. Yu. Smirnov, S. L. Ioffe, Yu. A. Strelenko, V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 1994, 1620 [Russ. Chem. Bull. (Engl. Transl.), 1994, 43, 1532].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2003–2008, October, 2011.
For Part 1, see Ref. 1.
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Klenov, M.S., Zelenov, V.P., Churakov, A.M. et al. Generation of oxodiazonium ions 2. Synthesis of benzotetrazine-1,3-dioxides from 2-(tert-butyl-NNO-azoxy)-N-nitroanilines. Russ Chem Bull 60, 2040–2045 (2011). https://doi.org/10.1007/s11172-011-0310-9
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DOI: https://doi.org/10.1007/s11172-011-0310-9