The substitution of pyrazolyl moiety in 3-(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine with N-nucleophiles provided a series of highnitrogen tetrazine derivatives, including 2-nitro-1-(1,2,4,5-tetrazin-3-yl)guanidine, N-(1H-tetrazol-5-yl)-1,2,4,5-tetrazin-3-amine, N-(1,2,4,5-tetrazin-3-yl)-1,2,4,5-tetrazin-3-amine, N,N'-di(1,2,4,5-tetrazin-3-yl)-1,2,4,5-tetrazine-3,6-diamine, N-(1,2,4,5-tetrazin-3-yl)-[1, 2, 4]triazolo[4,3-b][1, 2, 4, 5]tetrazin-6-amine, and tritetrazinylamine. The thermal stability of these new compounds was evaluated by differential scanning calorimetry and their energetic characteristics were calculated.
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(a) Tolshchina, S. G.; Rusinov, G. L.; Charushin, V. N. Chem. Heterocycl. Compd. 2013, 49, 66. [Khim. Geterotsikl. Soedin. 2013, 75.] (b) Knall, A.-C.; Slugovc, C. Chem. Soc. Rev. 2013, 42, 5131. (c) Prokhorov, A. M.; Kozhevnikov, D. N. Chem. Heterocycl. Compd. 2012, 48, 1153. [Khim. Geterotsikl. Soedin. 2012, 1237.] (d) Clavier, G.; Audebert, P. Chem. Rev. 2010, 110, 3299. (e) Stanovnik, B.; Grošelj, U.; Svete, J. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: New York, 2008, Vol. 9, p. 641. (f) Saracoglu, N. Tetrahedron 2007, 63, 4199. (g) Bohler, M. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Weinrib, S. M., Ed.; Georg Thieme Verlag: Stuttgart, 2006, Vol. 117, p. 585. (h) Kaim, W. Coord. Chem. Rev. 2002, 230, 126. (i) Neunhöffer, H. In Houben-Weyl Methods of Organic Chemistry; Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, 1998, Vol. E9c, p. 870. (j) Sauer, J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, Vol. 6, p. 901. (k) Sauer, J. Chem. Heterocycl. Compd. 1995, 31, 1140. [Khim. Geterotsikl. Soedin. 1995, 1307.] (l) Neunhöffer, H. In Comprehensive Heterocyclic Chemistry I; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, Vol. 3, p. 531. (m) Kovalev, E. G.; Postovskii, I. Ya.; Rusinov, G. L.; Shegal, I. L. Chem. Heterocycl. Compd. 1981, 17, 1063. [Khim. Geterotsikl. Soedin. 1981, 1462.] (n) Wiley, P. F. In The Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; John Wiley & Sons: New York, 1978, Vol. 33, p. 1073.
(a) Wei, T.; Zhu, W.; Zhang, X.; Li, Y.-F.; Xiao, H. J. Phys. Chem. A 2009, 113, 9404. (b) Zhou, Y.; Long, X.; Shu, Y. J. Mol. Model. 2010, 16, 1021. (c) Wei, T.; Wu, J.; Zhu, W.; Zhang, C.; Xiao, H. J. Mol. Model. 2012, 18, 3467. (d) Ghule, V. D.; Sarangapani, R.; Jadhav, P. M.; Tewari, S. P. Bull. Korean Chem. Soc. 2012, 33, 564. (e) Li, X.; Zhang, R.-Z.; Zhang, X.-Z. Struct. Chem. 2013, 24, 393. (f) Nabati, M.; Mahkam, M. Iran. J. Org. Chem. 2014, 6, 1397.
(a) Sinditskii, V. P.; Egorshev, V. Y.; Rudakov, G. F.; Filatov, S. A.; Burzhava, A. V. In Chemical Rocket Propulsion (A Comprehensive Survey of Energetic Materials); DeLuca, L. T.; Shimada, T.; Sinditskii, V. P.; Calabro, M., Eds.; Springer, 2017, p. 89. (b) McGrane, S. D.; Bolme, C. A.; Greenfield, M. T.; Chavez, D. E.; Hanson, S. K.; Scharff, R. J. J. Phys. Chem. A 2016, 120, 895. (c) Myers, T. W.; Brown, K. E.; Chavez, D. E.; Scharff, R. J.; Veauthier, J. M. Eur. J. Inorg. Chem. 2016, 3178. (d) Myers, T. W.; Brown, K. E.; Chavez, D. E.; Scharff, R. J.; Veauthier, J. M. Chem.–Eur. J. 2016, 22, 10590. (e) Chavez, D. E.; Parrish, D. A.; Mitchell, L. Angew. Chem., Int. Ed. 2016, 55, 1. (f) Aizikovich, A.; Shlomovich, A.; Cohen, A.; Gozin, M. Dalton Trans. 2015, 44, 13939. (g) Fu, Z.; Wang, Y.; Yang, L.; Su, R.; Chen, J.; Nie, F.; Huang, J.; Chen, F-X. RSC Adv. 2014, 4, 11859. (h) Zhang, Q.; He, C.; Yin, P.; Shreeve, J. M. Chem.–Asian J. 2014, 9, 212. (i) Chavez, D. E.; Hanson, S. K.; Veauthier, J. M.; Parrish, D. A. Angew. Chem., Int. Ed. 2013, 52, 1. (j) Sinditskii, V. P.; Egorshev, V. Yu.; Rudakov, G. F.; Burzhava, A. V.; Filatov, S. A.; Sang, L. D. Thermochim. Acta 2012, 535, 10, 48. (k) Gobel, M.; Klapotke, T. M. Adv. Funct. Mater. 2009, 19, 347. (l) Chavez, D. E.; Gilardi, R. D. J. Energ. Mater. 2009, 27, 110. (m) Chavez, D. E.; Parrish, D. A. J. Heterocycl. Chem. 2009, 46, 88. (n) Chavez, D. E.; Tappan, B. C.; Mason, B. A. Propellants, Explos., Pyrotech. 2009, 34, 475. (o) Duddu, R.; Dave, P. R.; Damavarapu, R.; Surapaneni, R.; Gilardi, R.; Parrish, D. Synth. Commun. 2008, 38, 767. (p) Chavez, D. E.; Hiskey, M. A.; Huynh, M. H. V.; Naud, D. L.; Son, S. F.; Tappan, B. C. J. Pyrotech. 2006, 23, 70. (q) Gao, H.; Wang, R.; Twamley, B.; Hiskey, M. A., Shreeve, J. M. Chem. Commun. 2006, 4007. (r) Chavez, D. E.; Tappan, B. C.; Hiskey, M. A.; Son, S. F.; Harry, H. H.; Montoya, D.; Hagelberg, S. Propellants, Explos., Pyrotech. 2005, 30, 412. (s) Loebbecke, S.; Schuppler, H.; Schweikert, W. J. Therm. Anal. Calorim. 2003, 72, 453. (t) Kerch, J.; Loebbecke, S. Propellants, Explos., Pyrotech. 2002, 27, 111. (u) Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Angew. Chem., Int. Ed. 2000, 39, 1791. (v) Chavez, D. E.; Hiskey, M. A. J. Energ. Mater. 1999, 17, 357. (w) Licht, H.-H.; Ritter, H. J. Energ. Mater. 1994, 12, 223.
(a) Benson, S. C.; Lee, L.; Yang, L.; Snyder, J. K. Tetrahedron 2000, 56, 1165. (b) Sauer, J.; Heldmann, D. K. Tetrahedron 1998, 54, 4297. (c) Marcelis, A. T. M.; van der Plas, H. C. Heterocycles 1985, 23, 683. (d) Müller, K.; Sauer, J. Tetrahedron Lett. 1984, 25, 2541. (e) Meresz, O.; Foster Verner, P. A. Chem. Commun. 1972, 950. (f) Adam, W.; van Barneveld, C.; Golsch, D. Tetrahedron 1996, 52, 2377.
(a) Lang, S. A.; Johnson, B. D.; Cohen, E.; Sloboda, A. E.; Greenblatt, E. J. Med. Chem. 1976, 19, 1404. (b) Lang, S. A.; Cohen, E.; Sloboda, A. E. US Patent 3863010.
(a) Chavez, D. E.; Hiskey, M. A. J. Heterocycl. Chem. 1998, 35, 1329. (b) Johnson, C. E.; Higa, K. T. US Patent 8801878.
(a) Devaraj, N. K.; Weissleder, R. Acc. Chem. Res. 2011, 44, 816. (b) Yang, K. S.; Budin, G.; Reiner, T.; Vinegoni, C.; Weissleder, R. Angew. Chem., Int. Ed. 2012, 51, 6598. (c) Carlson, J. C. T.; Meimetis, L. G.; Hilderbrand, S. A.; Weissleder, R. Angew. Chem., Int. Ed. 2013, 52, 6917. (d) Yang, K. S.; Budin, G.; Tassa, C.; Kister, O.; Weissleder, R. Angew. Chem., Int. Ed. 2013, 52, 10593. (e) Zeglis, B. M.; Emmetiere, F.; Pillarsetty, N.; Weissleder, R.; Lewis, J. S.; Reiner, T. ChemistryOpen 2014, 3, 48. (f) Zlitni, A.; Janzen, N.; Foster, F. S.; Valliant, J. F. Angew. Chem., Int. Ed. 2014, 53, 6459.
(a) Yang, J.; Karver, M. R.; Li, W.; Sahu, S.; Devaraj, N. K. Angew. Chem., Int. Ed. 2012, 51, 5222. (b) Alge, D. L.; Donohue, D. F.; Anseth, K. S. Tetrahedron Lett. 2013, 54, 5639. (c) Bowie, R. A.; Gardner, M. D.; Neilson, D. G.; Watson, K. M.; Mahmood, S.; Ridd, V. J. Chem. Soc., Perkin Trans. 1 1972, 2395. (d) Lang, S. A.; Johnson, B. D.; Cohen, E. J. Heterocycl. Chem. 1975, 12, 1143. (e) Counotte-Potman, A.; van der Plas, H. C. J. Heterocycl. Chem. 1981, 18, 123.
(a) Mangia, A.; Bortesi, F.; Amendola, U. J. Heterocycl. Chem. 1977, 14, 587. (b) Counotte-Poutman, A. D.; van der Plas, H. C. J. Heterocycl. Chem. 1978, 15, 445.
Grakauskas, V. A.; Tomasewski, A. J.; Horwitz, J. P. J. Am. Chem. Soc. 1958, 80, 3155.
Chavez, D. E.; Hiskey, M. A.; Gilardi, R. D. Org. Lett. 2004, 6, 2889.
(a) Chavez, D. E.; Hiskey, M. A.; Naud, D. L. Propellants, Explos., Pyrotech. 2004, 29, 209. (b) Saikia, A.; Sivabalan, R.; Polke, B. G.; Gore, G. M.; Amarjit Singh, Subhananda Rao, A.; Sikder, A. K. J. Hazard. Mater. 2009, 170, 306.
Counotte-Potman, A.; van der Plas, H. C.; van Veldhuizen, B.; Landeer, C. A. J. Org. Chem. 1981, 46, 5102.
Sheremetev, A. B.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu. Mendeleev Commun. 2012, 22, 302.
Rudakov, G. F.; Ustinova, T. V.; Kozlov, I. B.; Zhilin, V. F. Chem. Heterocycl. Compd. 2014, 50, 53. [Khim. Geterotsikl. Soedin. 2014, 59.]
(a) Ma̧kosza, M.; Wojciechowski, K. Chem. Rev. 2004, 104, 2631. (b) Ma̧kosza, M. Chem.–Eur. J. 2014, 20, 1. (c) Gulevskaya, A. V.; Tyaglivaya, I. N. Russ. Chem. Bull., Int. Ed. 2012, 61, 1321. [Izv. Akad. Nauk, Ser. Khim. 2012, 1307.]
Palysaeva, N. V.; Kumpan, K. P.; Struchkova, M. I.; Dalinger, I. L.; Kormanov, A. V.; Aleksandrova, N. S.; Chernyshev, V. M.; Pyreu, D. F.; Suponitsky, K. Yu.; Sheremetev, A. B. Org. Lett. 2014, 16, 406.
Sheremetev, A. B.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu.; Antipin, M. Yu. Eur. J. Org. Chem. 2012, 2266.
(a) Yao, W.; Kavallieratos, K.; Gala, S.; Crabtree, R. H. Inorg. Chim. Acta 2000, 311, 45. (b) Fukushima, Y.; Nohara, N.; Nashida, Y.; Sekiguchi, S.; Matsui, K. Bull. Chem. Soc. Jpn. 1971, 44, 794. (c) Nohara, N.; Sekiguchi, S.; Matsui, K. J. Heterocycl. Chem. 1970, 7, 519. (d) Mosny, K. K.; Crabtree, R. H. Inorg. Chim. Acta 1996, 247, 93.
(a) Sheremetev, A. B.; Kulagina, V. O.; Yudin, I. L.; Kuzmina, N. E. Mendeleev Commun. 2001, 11, 112. (b) Ghule, V. D.; Deswal, S.; Devi, A.; Kumar, T. R. Ind. Eng. Chem. Res. 2016, 55, 875.
(a) Amoore, J. J. M.; Kepert, C. J.; Cashion, J. D.; Moubaraki, B.; Neville, S. M.; Keith S.; Murray, K. S. Chem.–Eur. J. 2006, 12, 8220. (b) McWhinnie, W. R.; Kulasingam, G. C.; Draper, J. C. J. Chem. Soc. A 1966, 1199.
(a) Sigworth, W. D.; Pace, E. L. Spectrochim. Acta, Part A 1971, 27, 747. (b) Martin, J. M. L.; van Alsenoy, C. J. Phys. Chem. 1996, 100, 6973.
(a) Oxley, J. C.; Smith, J. L.; Zhang, J. J. Phys. Chem. A 2000, 104, 6764. (b) Sheremetev, A. B.; Palysaeva, N. V.; Suponitsky, K. Yu.; Struchkova, M. I. Russ. Chem. Bull., Int. Ed. 2012, 61, 121. [Izv. Akad. Nauk, Ser. Khim. 2012, 119.]
Sućeska, M. EXPLO 5.06 program; Zagreb, 2013.
Kotomin, A. А.; Kozlov, А. S. Density of Organic Compounds. Method for the Calculation of Density from the Contributions of Molecular Fragments [in Russian]; Izd-vo SPbGTI (TU): St. Petersburg, 2005.
Wai, H.; Gao, H.; Shreeve, J. M. Chem.–Eur. J. 2014, 20, 16943.
Coburn, M. D.; Buntain, G. A.; Harris, B. W.; Hiskey, M. A.; Lee, K.-Y.; Ott, D. G. J. Heterocycl. Chem. 1991, 28, 2049.
Latosh, N. I.; Rusinov, G. L.; Ganebnykh, I. N.; Chupakhin, O. N. Russ. J. Org. Chem. 1999, 35, 1363. [Zh. Org. Khim. 1999, 1392.]
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 802–810
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Rudakov, G.F., Moiseenko, Y.A. & Spesivtseva, N.А. Synthesis of monosubstituted 1,2,4,5-tetrazines – 3-amino-1,2,4,5-tetrazines. Chem Heterocycl Comp 53, 802–810 (2017). https://doi.org/10.1007/s10593-017-2127-4
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DOI: https://doi.org/10.1007/s10593-017-2127-4