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Nitration of 3-amino-4-(1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles (3-amino-4-triazolylfurazans) with a mixture of NaNO3 and conc. H2SO4 gave for the first time triazolylfurazans with a primary nitramino group attached to the furazan ring. If the starting amino(triazolyl)-furazan contains an aromatic substituent, the latter also undergoes nitration under the conditions studied. Some of these nitramines were converted into salts (K, Na, and NH4).
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L. V. Batog, L. S. Konstantinova, V. Yu. Rozhkov, Yu. A. Strelenko, O. V. Lebedev, L. I. Khmelnitskii, Khim. Geterotsikl. Soedin., 2000, 100 [Chem. Heterocycl. Compd. (Engl. Transl.), 2000, 36, 91].
L. V. Batog, V. Yu. Rozhkov, M. I. Struchkova, Mendeleev Commun., 2002, 159.
P. H. Olesen, A. R. Sorensen, B. Urso, P. Kurtzhals, A. N. Bowler, U. Ehrbar, B. F. Hansen, J. Med. Chem., 2003, 46, 3333.
V. Yu. Rozhkov, L. V. Batog, E. K. Shevtsova, M. I. Struchkova, Mendeleev Commun., 2004, 76.
V. Yu. Rozhkov, L. V. Batog, M. I. Struchkova, Izv. Akad. Nauk, Ser. Khim., 2005, 1866 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1923].
L. V. Batog, L. S. Konstantinova, V. Yu. Rozhkov, Izv. Akad. Nauk, Ser. Khim., 2005, 1859 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1915].
A. B. Sheremetev, Ross. Khim. Zh. (Zh. Ross. Khim. O-va im. D. I. Mendeleeva), 1997, 2, 43 [Mendeleev Chem. J. (Engl. Transl.), 1997, 41, 62].
I. V. Tselinskii, S. F. Mel’nikova, S. N. Vergizov, Zh. Org. Khim., 1995, 31, 1234 [Russ. J. Org. Chem. (Engl. Transl.), 1995, 31].
V. P. Zelenov, A. A. Lobanova, A. A. Voronin, A. M. Churakov, Tezisy dokladov Vserossiiskoi konferentsii “Khimiya nitrosoedinenii i rodstvennykh azot—kislorodnykh sistem” [Abstrs, All-Russia Conf. “The Chemistry of Nitro Compounds and Related N—O Systems”], Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, 2009 (in Russian).
V. Yu. Rozhkov, L. V. Batog, Sintezy organicheskikh soedinenii [Syntheses of Organic Compounds], Issue 3, Ed. M. P. Egorov, MAKS Press, 2008, 197 (in Russian).
V. Yu. Rozhkov, L. V. Batog, Materialy IV Vserossiiskoi konferentsii “Energeticheskie kondensirovannye sistemy” [Proc. IV All-Russia Conf. “High-Energy Fused Systems”] (November 12–14, 2008, Chernogolovka), Chernogolovka, 2008, 154 (in Russian).
A. B. Sheremetev, V. O. Kulagina, N. S. Aleksandrova, T. S. Novikova, L. I. Khmelnitskii, in Proc. 3 th Int. Symp. on Pyro- technics and Explosives, China Academic Publishing, Beijing, 1995, 249.
V. A. Frolovskii, V. A. Petrosyan, Izv. Akad. Nauk, Ser. Khim., 1999, 1935 [Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 1911].
S. D. Shaposhnikov, T. M. Romanova, N. P. Spiridonova, S. F. Mel’nikova, I. V. Tselinskii, Zh. Org. Khim., 2004, 40, 922 [Russ. J. Org. Chem. (Engl. Transl.), 2004, 40].
A. V. Sergievskii, T. V. Romanova, O. F. Mel’nikova, I. V. Tselinskii, Zh. Org. Khim., 2005, 41, 270 [Russ. J. Org. Chem. (Engl. Transl.), 2005, 41].
A. M. Churakov, S. E. Semenov, S. L. Ioffe, Y. A. Strelenko, V. A. Tartakovsky, Mendeleev Commun., 1995, 102.
K. Yu. Suponitskii, K. A. Lyssenko, M. Yu. Antipin, N. S. Aleksandrova, A. B. Sheremetev, T. S. Novikova, Izv. Akad. Nauk, Ser. Khim., 2009, 2065 [Russ. Chem. Bull., Int. Ed., 2009, 58, 2129].
L. V. Batog, V. Yu. Rozhkov, Yu. A. Strelenko, O. V. Lebedev, L. I. Khmelnitskii, Khim. Geterotsikl. Soedin., 2000, 406 [Chem. Heterocycl. Compd. (Engl. Transl.), 2000, 36, 343].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1687–1692, August, 2011.
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Rozhkov, V.Y., Batog, L.V. & Struchkova, M.I. Synthesis of 3-nitramino-4-(1H-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles and their salts. Russ Chem Bull 60, 1712–1718 (2011). https://doi.org/10.1007/s11172-011-0255-z
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DOI: https://doi.org/10.1007/s11172-011-0255-z