Abstract
Alkylation of 5-aminotetrazole with chloromethylnitrazaalkanes led to 1-nitrazaalkyl derivatives, which reacted with formalin solution and sodium carbonate followed by treatment with nitroform to form 1-nitrazaalkyl-5-(1,1,1-trinitro-3-azapropyl)tetrazoles. The latter were nitrated for the first time to obtain tetrazoles containing both trinitromethyl and nitrazaalkyl groups.
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L. Schischkoff, Ann. Chem., 1857, 103, 364; DOI: https://doi.org/10.1002/jlac.18571030316.
New Trends in Research of Energetic Materials, Proc. of the 22th Seminar, Pardubice (Czech Republic, April 9–11, 2019).
T. S. Kon’kova, Yu. N. Matyushin, E. A. Miroshnichenko, A. B. Vorob’ev, O. A. Luk’yanov, G. A. Smirnov, Goreniye i vzryv [Combustion and Explosion], 2018, 11, 113 (in Russian).
Y. A. Volkova, E. B. Averina, Y. K. Grishin, P. Bruheim, T. S. Kuznetsova, N. S. Zefirov, J. Org. Chem., 2010, 75, 3047; DOI: https://doi.org/10.1021/jo100319p.
Y. A. Volkova, E. B. Averina, D. A. Vasilenko, K. N. Sedenkova, Y. K. Grishin, P. Bruheim, T. S. Kuznetsova, N. S. Zefirov, J. Org. Chem., 2019, 84, 3192; DOI: https://doi.org/10.1021/acs.joc.8b03086.
Q. J. Axthammer, B. Krumm, T. M. Klapötke, J. Org. Chem., 2015, 80, 6329; DOI: https://doi.org/10.1021/acs.joc.5b00655.
H. Gao, J. M. Shreeve, RSC Adv., 2014, 4(47), 24874; DOI: https://doi.org/10.1039/C4RA03885A.
Y. Li, H. Huang, X. Lin, R. Pan, J. Yang, RSC Adv., 2016, 6(59), 54310; DOI: https://doi.org/10.1039/C6RA10756G.
T. M. Klapötke, B. Krumm, R. Scharf, Zeit. Anorg. Allg. Chem., 2016, 642(16), 887; DOI: https://doi.org/10.1002/zaac.201600223.
T. M. Klapötke, B. Krumm, R. Moll, A. Penger, S. M. Sproll, R. J. F. Berger, S. A. Hayes, N. W. Mitzel, Zeit. Naturforsch. B: J. Chem. Sci., 2013, 68, 719; DOI: https://doi.org/10.5560/ZNB.2013-2311.
T. M. Klapötke, B. Krumm, R. Moll, S. F. Rest, W. Schnick, M. Seibald, J. Fluorine Chem., 2013, 156, 253; DOI: https://doi.org/10.1016/j.jfluchem.2013.06.019.
A. A. Gakh, J. C. Bryan, M. N. Burnett, P. V. Bonnesen, J. Mol. Struct., 2000, 520, 221; DOI: https://doi.org/10.1016/S0022-2860(99)00333-6.
S. S. Novikov, V. I. Slovetskii, S. A. Shevelev, A. A. Fainzilberg, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1962, 11, 552; DOI: https://doi.org/10.1007/BF00904751.
H. F. R. Schoyer, W. H. M. Welland-Veltman, J. Louwers, P. A. O. G. Korting, A. E. D. M. van der Heijden, H. L. J. Keizers, R. P. van den Berg, J. Propulsion Power, 2002, 18, 131; DOI: https://doi.org/10.2514/2.5908.
D. A. Vasilenko, K. S. Sadovnikov, K. N. Sedenkova, D. S. Karlov, E. V. Radchenko, Y. K. Grishin, V. B. Rybakov, T. S. Kuznetsova, V. L. Zamoyski, V. V. Grigoriev, V. A. Palyulin, E. B. Averina, Molecules, 2021, 26, 6411, DOI: https://doi.org/10.3390/molecules26216411.
T. M. Klapötke, Chemistry of High-Energy Materials, 4th ed., De Gruyter, Berlin, Germany, 2015.
T. M. Klapötke, B. Krumm, R. Scharf, Eur. J. Inorg. Chem., 2016, 19, 3086; DOI: https://doi.org/10.1002/ejic.201600357.
E. T. Apasov, A. V. Kalinin, S. L. Ioffe, V. A. Tartakovskii, Russ. Chem. Bull., 1993, 42, 1262; DOI: https://doi.org/10.1007/BF00702022.
P. Yin, Q. Zhang, J. Zhang, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A, 2013, 1, 7500; DOI: https://doi.org/10.1039/c3ta11356f.
D. E. Chavez, D. A. Parrish, L. Mitchell, Angew. Chem., Int. Ed., 2016, 55, 8666; DOI: https://doi.org/10.1002/anie.201604115.
A. G. Korepin, A. V. Shastin, N. M. Glushakova, V. P. Kosilko, V. S. Malygina, G. V. Lagodzinskaya, V. P. Lodygina, Russ. Chem. Bull., 2019, 68, 610; DOI: https://doi.org/10.1007/s11172-019-2463-x.
C. Yan, G. Cheng, K. Wang, T. Liu, Y. Jin, H. Yang, Q. Zhang, New J. Chem., 2019, 43, 10429; DOI: https://doi.org/10.1039/C9NJ01932D.
T. M. Klapötke, B. Krumm, T. Reith, C. C. Unger, J. Org. Chem., 2018, 83, 10505; DOI: https://doi.org/10.1021/acs.joc.8b01072.
Q. Yu, Z. Wang, H. Yang, B. Wu, Q. Lin, X. Ju, C. Lu, G. Cheng, RSC Adv., 2015, 5, 27305; DOI: https://doi.org/10.1039/C5RA03230J.
Pat. RU 2615630 C1; Byul. Izobret. [Invention Bull.], 2017 (in Russian).
D. E. Chavez, M. C. Schulze, D. A. Parrish, Chem. Heterocycl. Compd., 2017, 53, 737; DOI: https://doi.org/10.1007/s10593-017-2119-4.
D. E. Chavez1, T. M. Klapötke, D. A. Parrish, D. G. Piercey, J. Stierstorfer, Propellants, Explos., Pyrotech., 2014, 39, 641; DOI: https://doi.org/10.1002/prep.201300135.
M. A. Epishina, A. O. Finogenov, A. S. Kulikov, N. N. Makhova, I. V. Anan’ev, V. A. Tartakovskii, Russ. Chem. Bull., 2012, 61, 1575; DOI: https://doi.org/10.1007/s11172-012-0209-0.
X. Zhen, G. Cheng, H. Yang, J. Zhang, J. M. Shreeve, Chem. Eur. J., 2018, 24, 10488; DOI: https://doi.org/10.1002/chem.201801597.
V. Thottempudi, P. Yin, J. Zhang, D. A. Parrish, J. M. Shreeve, Chem. Eur. J., 2014, 20, 542; DOI: https://doi.org/10.1002/chem.201303469.
M. M. Krayushkin, V. V. Sevost’yanova, V. N. Yarovenko, I. V. Zavarzin, Russ. Chem. Bull., 2009, 58, 2175; DOI: https://doi.org/10.1007/s11172-009-0298-6.
O. A. Lukyanov, N. I. Shlykova, G. V. Pokhvisneva, T. V. Ternikova, S. V. Nikitin, G. A. Smirnov, Y. V. Nelubina, P. V. Dorovatovskii, T. S. Konkova, N. V. Muravyov, A. N. Pivkina, Russ. Chem. Bull., 2017, 66, 1066; DOI: https://doi.org/10.1007/s11172-017-1855-z.
O. A. Lukyanov, N. I. Shlykova, G. V. Pokhvisneva, T. V. Ternikova, K. A. Monogarov, D. B. Meerov, Y. V. Nelubina, P. V. Dorovatovskii, T. S. Konkova, Russ. Chem. Bull., 2019, 68, 110; DOI: https://doi.org/10.1007/s11172-019-2424-4.
N. Fischer, K. Karaghiosoff, T. M. Klapötke, J. Stierstorfer, Z. Anorg. Allg. Chem., 2010, 636, 735; DOI: https://doi.org/10.1002/zaac.200900521.
R. N. Butler, T. M. Mebvoy, F. L. Scott, J. C. Fobin, Can. J. Chem., 1977, 55, 1564; DOI: https://doi.org/10.1139/v77-217.
J. Elquere, C. Mazzin, J. D. Roberts, J. Org. Chem., 1974, 39, 357; DOI: https://doi.org/10.1021/jo00917a017.
A. Kennecke, E. Lippmann, E. Kleinpetes, Tetrahedron Lett., 1976, 17, 533; DOI: https://doi.org/10.1016/S0040-4039(00)77903-2.
B. R. Reed, J. Am. Chem. Soc., 1956, 78, 801.
B. Wojciech, J. Jazwinski, W. Kozminski, L. Stefaniak, G. A. Webb, J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem., 1994, 6, 1327.
S. S. Novikov, Z. Ya. Lapshina, B. A. Rudenko, L. S. Semenenok, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1960, 9, 1211; DOI: https://doi.org/10.1007/BF01161553.
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Dedicated to the Academician of the Russian Academy of Sciences V. A. Tartakovsky on the occasion of his 90th birthday.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1981–1986, September, 2022.
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Krayushkin, M.M., Chernoburova, E.I. & Zavarzin, I.V. Synthesis of 1-nitrazaalkyl-5-(1,1,1-trinitro-3-nitrazapropyl)tetrazoles. Russ Chem Bull 71, 1981–1986 (2022). https://doi.org/10.1007/s11172-022-3617-9
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DOI: https://doi.org/10.1007/s11172-022-3617-9