This review covers the methods applicable for the synthesis of (dinitromethyl)azines: nitration of azine derivatives, azine ring formation,nucleophilic su bstitution in azine rings by the action of dinitrocarbanions, and denitration of trinitromethylazines. Further reactions with the conservation of dinitromethyl group, as well as its transformations into other functional groups, or modification of other substituents in (dinitromethyl)azines are also considered. Dinitromethylazines are of interest as energetic materials with low sensitivity and as biologically active compounds.
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(a) Shastin, A. V.; Godovikova, T.; Korsunskii, B. Russ. Chem. Rev. 2003, 72, 279. [Usp. Khim. 2003, 311.] (b) Bellamy, A. J.; Latypov, N. V.; Goede, P. J. Chem. Res., Synop. 2003, 529. (c) Gidaspov, A. A.; Bakharev, V. V.; Kukushkin, I. K. Russ. Chem. Bull., Int. Ed. 2009, 58, 2154. [Izv. Akad. Nauk, Ser. Khim. 2009, 2089.] (d) Shastin, A. V.; Godovikova, T. I.; Golova, S. P.; Kuz'min, V. S.; Khmel'nitskii, L. I.; Korsunskii, B. L. Mendeleev Commun. 1995, 5, 17. (e) Shastin, A. V.; Godovikova, T. I.; Korsunskii, B. L. Russ. Chem. Bull., Int. Ed. 2011, 60, 1220. [Izv. Akad. Nauk, Ser. Khim. 2011, 1194.] (f) Bakharev, V. V.; Gidaspov, A. А.; Peresedova, E. V. Vestn. Sam. Gos. Tekhn. Un-ta. Ser. Tekhn. Nauki 2006, 154. (g) Bakharev, V. V.; Gidaspov, A. A.; Kachanovskaya, E. V. Russ. J. Org. Chem. 2007, 43, 454. [Zh. Org. Khim. 2007, 43, 455.] (h) Gidaspov, A. A. In Proceedings of the 10th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2007, p. 602. (i) Gidaspov, A. A. In Proceedings of the 10th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2007, p. 600. (j) Gidaspov, А. А.; Burkov, P. S.; Kuleshova, I. A.; Bakharev, V. V. Vestn. SamGU 2012, 159. (k) Bakharev, V. V.; Gidaspov, A. A. In Proceedings of the 11th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2008, p. 461. (l) Gidaspov, A. A. In Proceedings of the 11th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2008, p. 539. (m) Bakharev, V. V.; Gidaspov, A. A.; Ul'yankina, I. V. In Proceedings of the 13th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2010, p. 404. (n) Gidaspov, A. A.; Bakharev, V. V.; Kukushkin, I. K.; Zalomlenkov, V. A.; Burkov, P. S. In Proceedings of the 13th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2010, p. 492. (o) Gidaspov, A. A.; Bakharev, V. V. In Proceedings of the 15th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2012, p. 589. (p) Gidaspov, A. A.; Bakharev, V. V.; Zalomlenkov, V. A.; Burkov, P. S.; Artemyeva, I. I.; Kuleshova, I. A. In Proceedings of the 16th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2013, p. 605. (q) Gidaspov, A. A.; Bakharev, V. V.; Zalomlenkov, V. A.; Burkov, P. S.; Shaposhnikov, M. N.; Bayzarov, D. A. In Proceedings of the 16th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2013, p. 609.
Rubtsov, M. V.; Nikitskaya, E. S.; Usovskaya, V. S. Russ. J. Gen. Chem. 1955, 25, 2453. [Zh. Obshch. Khim. 1955, 2453.]
Rubinstein, H.; Hazen, G.; Zerfing, R. C. J. Chem. Eng. Data 1967, 12, 149.
Luk'yanov, O. A.; Zhiguleva, T. I. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1982, 31, 1270. [Izv. Akad. Nauk SSSR, Ser. Khim. 1982, 1423.]
(a) Astrat'ev, A. A.; Dashko, D. V.; Mershin, A. Y.; Stepanov, A. I.; Urazgil'deev, N. A. Russ. J. Org. Chem. 2001, 37, 729. [Zh. Org. Khim. 2001, 37, 766.] (b) Chung, K.-H.; Goh, E. M.; Cho, J. R. In 36th International Annual Conference ICT; Karlsruhe, 2005, p. 52(1). (c) Chylek, Z.; Cudzilo, S.; Bladek, J.; Pietrzyk, S. In Proceedings of the 8th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2005, p. 211. (d) Bellamy, A. J.; Latypov, N. V.; Goede, P. In Proceedings of the 7th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2004, p. 74.
(a) Shastin, A.; Godovikova, T.; Golova, S.; Khmel'nitskii, L.; Korsunskii, B. Chem. Heterocycl. Compd. 1997, 33, 1095. [Khim. Geterotsikl. Soedin. 1997, 1254.] (b) Shastin, A.; Godovikova, T.; Korsunskii, B. Chem. Heterocycl. Compd. 1999, 35, 72. [Khim. Geterotsikl. Soedin. 1999, 76.]
(a) Astrat'ev, A. A.; Dashko, D. V.; Stepanov, A. I. In Proceedings of the 14th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2011, p. 468. (b) Gao, H.; Shreeve, J. n. M. Angew. Chem., Int. Ed. 2015, 54, 6335.
Golovina, O. V.; Bakharev, V. V.; Golovin, E. V.; Parfenov, V. E.; Slepukhin, P. A. Tetrahedron Lett. 2013, 54, 3858.
Fokin, A. V.; Studnev, Y. N.; Kuznetsova, L. D. Russ. Chem. Bull. 1996, 45, 1952. [Izv. Akad. Nauk, Ser. Khim. 1996, 2056.].
Koppes, W. M.; Adolph, H. G. J. Org. Chem. 1981, 46, 406.
(a) Onishchenko, A. A.; Ternikova, T. V.; Luk'yanov, O. A.; Tartakovskii, V. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1975, 24, 2227. [Izv. Akad. Nauk SSSR, Ser. Khim. 1975, 2342.] (b) Onishchenko, A. A.; Ternikova, T. V.; Luk'yanov, O. A.; Tartakovskii, V. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1976, 25, 2356. [Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 2530.]
Gidaspov, А. А.; Bakharev, V. V. In III All-Russia Conference “Energetic Condensed Systems” [in Russian]; Yanus-K: Chernogolovka, 2006, p. 27.
(a) Bakharev, V. V. Dissertation of Doctor of Chemical Sciences; Samara, 2008. (b) Shastin, A. V.; Godovikova, T. I.; Golova, S. P.; Khmel'nitskii, L. I.; Korsunskii, B. L. Chem. Heterocycl. Compd. 1995, 31, 596. [Khim. Geterotsikl. Soedin. 1995, 674.] (c) Bakharev, V. V.; Gidaspov, А. А. Izv. SNTs RAN. Khimiya i Khim. Tekhnologiya 2004, 190. (d) Bakharev, V. V.; Gidaspov, А. А.; Peresedova, E. V. Izv. Vuzov. Khimiya i Khim. Tekhnologiya 2007, 50, 85. (e) Shastin, A. V.; Godovikova, T. I.; Korsunskii, B. L. Chem. Heterocycl. Compd. 2003, 39, 354. [Khim. Geterotsikl. Soedin. 2003, 400.] (f) Bakharev, V. V.; Gidaspov, A. A. In Proceedings of the 10th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2007, p. 517.
Meisenheimer, J.; Schwarz, M. Chem. Ber. 1906, 39, 2543.
(a) Hantzsch, A.; Rinckenberger, A. Chem. Ber. 1899, 32, (b) Meisenheimer, J. Chem. Ber. 1903, 36, 434.
Zeldin, L.; Shechter, H. J. Am. Chem. Soc. 1957, 79, 4708.
L'vova, M. S.; Slovetskii, V. I.; Fainzil'berg, A. A. Bull. Acad. Sci. USSR, Div. Chem. Sci 1966, 15, 615. [Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 649.].
Glover, D. J.; Kamlet, M. J. J. Org. Chem. 1961, 26, 4734.
(a) Glover, D. J. Tetrahedron 1963, 19, 219. (b) Macbeth, A. K.; Pratt, D. D. J. Chem. Soc., Trans. 1921, 119, 1356.
Glover, D. J. J. Org. Chem. 1964, 29, 990.
Parker, C. O.; Emmons, W. D.; Rolewicz, H. A.; McCallum, K. S. Tetrahedron 1962, 17, 79.
(a) Tartakovskii, V. A.; Chlenov, I. E.; Novikov, S. S. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1966, 15, 1778. [Izv. Akad. Nauk SSSR, Ser. Khim. 1966, 1842.] (b) Okhlobystina, L. V.; Legin, G. Y.; Fainzil'berg, A. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1969, 18, 2172. [Izv. Akad. Nauk SSSR, Ser. Khim. 1969, 2318.]
(a) Shastin, A. V.; Godovikova, T. I.; Golova, S. P.; Povorin, M. V.; Dmitriev, D. E.; Dekaprilevich, M. O.; Strelenko, Y. A.; Struchkov, Y. T.; Khmel'nitskii, L. I.; Korsunskii, B. L. Chem. Heterocycl. Compd. 1995, 31, 601. [Khim. Geterotsikl. Soedin. 1995, 679.] (b) Fedorov, B. S.; Fadeev, M. A.; Gidaspov, A. A.; Kosareva, E. A.; Bakharev, V. V. Chem. Heterocycl. Compd. 2005, 41, 228. [Khim. Geterotsikl. Soedin. 2005, 259.]
Novikov, S. S.; Khmel'nitskii, L. I.; Novikova, T. S.; Lebedev, O. V. Chem. Heterocycl. Compd. 1970, 6, 543. [Khim. Geterotsikl. Soedin. 1970, 590.].
Deady, L. W.; Quazi, N. H. Aust. J. Chem. 1992, 45, 2083.
(a) Bakharev, V. V.; Gidaspov, A. A.; Ekimova, E. V.; Galkina, M. V. In International Science-Engineering and Technical Conference “Current Problems of the Technical Chemistry”; Kazan, 2004, p. 273. (b) Bakharev, V. V.; Gidaspov, A. A.; Zalomlenkov, V. A.; Nazarova, I. S.; Palatova, Y. T. In Proceedings of the 14th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2011, p. 481.
(a) Gidaspov, A. A.; Bakharev, V. V.; Kachanovskaya, E. V.; Kosareva, E. A.; Galkina, M. V.; Ekimova, E. V.; Yakunina, N. G.; Bulychev, Y. N. Pharm. Chem. J. 2004, 38, 411. [Khim.-Farm. Zh. 2004, 38(8), 9.] (b) Gidaspov, A. A.; Bakharev, V. V.; Velikanova, E. V.; Tselinsky, I. V. In Proceedings of the 12th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2009, p. 539.
Gidaspov, A. A.; Bakharev, V. V.; Bulychev, Y. N. Pharm. Chem. J. 2000, 34, 342. [Khim.-Farm. Zh. 2000, 34(7), 6.]
(a) Gidaspov, A. A.; Bakharev, V. V.; Kachanovskaya, E. V.; Yakunina, N. G.; Bulychev, Y. N. Pharm. Chem. J. 2002, 36, 366. [Khim.-Farm. Zhurn. 2002, 36(7), 26.] (b) Bakharev, V. V.; Gidaspov, А. А.; Kosareva, E. A. Izv. Vuzov. Khimiya i Khim. Tekhnologiya 2004, 47, 138. (c) Bakharev, V. V.; Gidaspov, А. А. Izv. Vuzov. Khimiya i Khim. Tekhnologiya 2005, 48, 146. (d) Bakharev, V. V.; Gidaspov, А. А.; Kosareva Е. А. Izv. Vuzov. Khimiya i Khim. Tekhnologiya 2006, 49, 10.
Bakharev, V. V.; Gidaspov, A. A.; Zueva, M. A. Russ. J. Gen. Chem. 2006, 76, 1846. [Zh. Obshch. Khim. 2006, 1930.]
Srinivas, D.; Mitchell, L. A.; Parrish, D. A.; Shreeve, J. M. Chem. Commun. 2016, 52, 7668.
Li, Y.; Huang, H.; Lin, X.; Pan, R.; Yang, J. Dalton Trans. 2016, 45, 15644.
Slovetskii, V. I.; Khisamutdinov, G. K.; Petrosyan, V. A.; Orlova, É. K.; Fainzil'berg, A. A. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1972, 21, 1670. [Izv. Akad. Nauk SSSR, Ser. Khim. 1972, 1725.].
Gidaspov, A. A.; Bakharev, V. V.; Golovina, O. V.; Selezneva, E. V. In Proceedings of the 17th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2014, p. 653.
Bakharev, V. V.; Gidaspov, A. A.; Kosareva, E. A. J. Struct. Chem. 2007, 48, 181. [Zh. Strukt. Khim. 2007, 178.]
(a) Gidaspov, A. A.; Bakharev, V. V.; Pepekin, V. I.; Afanasiev, G. T.; Matushin, Y. N. In Proceedings of the 14th Seminar on New Trends in Research of Energetic Materials; Pardubice, 2011, p. 668. (b) Bakharev, V. V.; Gidaspov, A. A. Russ. J. Org. Chem. 2007, 43, 1238. [Zh. Org. Khim. 2007, 1241.]
(a) Bakharev, V. V.; Gidaspov, A. A.; Peresedova, E. V. Chem. Heterocycl. Compd. 2006, 42, 557. [Khim. Geterotsikl. Soedin. 2006, 635.] (b) Bakharev, V. V.; Gidaspov, A. A.; Peresedova, E. V. Chem. Heterocycl. Compd. 2006, 42, 1096. [Khim. Geterotsikl. Soedin. 2006, 1263.] (c) Bakharev, V. V.; Gidaspov, A. A.; Peresedova, E. V.; Granik, V. G.; Grigor'ev, N. B.; Levina, V. I.; Severina, I. S.; Shchegolev, A. Y.; Dmitriev, D. E.; Sheremetev, A. B. Russ. Chem. Bull., Int. Ed. 2009, 58, 1962. [Izv. Akad. Nauk, Ser. Khim. 2009, 1900.].
(s Russ. Chem. Bull. 1993, 42, 131. [Izv. Akad. Nauk, Ser. Khim. 1993, 147.] (b) Rakitin, O. A.; Ogurtsov, V. A.; Godovikova, T. I.; Khmel'nitskii, L. I. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990, 39, 1469. [Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 1620.]
(a) Bakharev, V.; Peresedova, E.; Krivolapov, D.; Mironova, E.; Litvinov, I. Chem. Heterocycl. Compd. 2009, 45, 587. [Khim. Geterotsikl. Soedin. 2009, 743.] (b) Bakharev, V. V.; Gidaspov, A. A.; Peresedova, E. V.; Krivolapov, D. B.; Mironova, E. V.; Litvinov, I. A. Chem. Heterocycl. Compd. 2009, 45, 1075. [Khim. Geterotsikl. Soedin. 2009, 1345.] (c) Bakharev, V. V.; Gidaspov, A. A.; Selezneva, E. V.; Ul'yankina, I. V.; Krivolapov, D. B.; Litvinov, I. A.; Eltsov, O. S. Chem. Heterocycl. Compd. 2011, 46, 1386. [Khim. Geterotsikl. Soedin. 2010, 1709.] (d) Bakharev, V. V.; Gidaspov, A. A.; Selezneva, E. V.; Parfenov, V. E.; Ul'yankina, I. V.; Nazarova, I. S.; Palatova, Y. T.; El'tsov, O. S. Chem. Heterocycl. Compd. 2012, 47, 1258. [Khim. Geterotsikl. Soedin. 2011, 1521.] (e) Bakharev, V. V.; Gidaspov, A. A.; Selezneva, E. V.; El'tsov, O. S. Chem. Heterocycl. Compd. 2012, 48, 912. [Khim. Geterotsikl. Soedin. 2012, 982.]
(a) Smirnov, S. P.; Smirnov, A. S. Russ. J. Appl. Chem. 2009, 82, 1807. [Zh. Prikl. Khim. 2009, 1655.] (b) Smirnov, A. S.; Lempert, D. B.; Pivina, T. S.; Khakimov, D. Cent. Eur. J. Energ. Mater. 2011, 8, 233.
Gidaspov, A. A.; Bakharev, V. V.; Fedorov, B. S.; Fadeev, M. A.; Konovalova, N. P. Russ. J. Appl. Chem. 2009, 82, 1816. [Zh. Prikl. Khim. 2009, 1664.]
Gidaspov, A. A.; Bakharev, V. V.; Kachanovskaya, E. V.; Bulychev, Y. N.; Levina, V. I.; Azizov, O. V.; Arzamastsev, A. P.; Grigor'ev, N. B.; Granik, V. G. Pharm. Chem. J. 2003, 37, 463. [Khim.-Farm. Zh. 2003, 37(9), 12.]
Malishev, B. S.; Evdokimov, A. А.; Netesova, N. A.; Maligin, E. G.; Bormotov, N. I.; Shishkina, L. N.; Gidaspov, А. А.; Bakharev, V. V.; Klimochkin, Yu. N. RU Patent 2541525; Byul. Izobret. 2015, (5).
Keshavarz, M. H. J. Hazard. Mater. 2007, 141, 536.
Bogdanova, Y.; Gubin, S.; Korsunskii, B.; Pepekin, V. Combust., Explos. Shock Waves 2009, 45, 738.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 659–669
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Bakharev, V.V., Gidaspov, A.A. & Parfenov, V.E. Chemistry of (dinitromethyl)azines. Chem Heterocycl Comp 53, 659–669 (2017). https://doi.org/10.1007/s10593-017-2107-8
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DOI: https://doi.org/10.1007/s10593-017-2107-8