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Synthesis and properties of 3-azido-4-(2H-tetrazol-5-yl)furazan

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Chemistry of Heterocyclic Compounds Aims and scope

We describe an effective scheme for the synthesis of a new energetic compound – 3-azido-4-(2H-tetrazol-5-yl)furazan from 4-amino-N'-hydroxyfurazan-3-carboximidamide. The structure of 3-azido-4-(2H-tetrazol-5-yl)furazan was proved by 1Н and 13С NMR spectroscopy, mass spectrometry, and X-ray structural analysis. 3-Azido-4-(2H-tetrazol-5-yl)furazan crystallized in monoclinic syngony, space group Р21/n, monocrystal density d 1.953 g·cm–3 (100 K). According to differential scanning calorimetry data, 3-azido-4-(2Htetrazol-5-yl)furazan melts at 103.3°С, while the maximum of thermal decomposition exotherm was observed at 185.6°С. The sensitivity of 3-azido-4-(2H-tetrazol-5-yl)furazan to impact (2 kg, 25 cm, 36% explosion frequency) and to friction (1450 kg·cm–3 lower limit) was at the level of pentaerythritol tetranitrate. The salts of 3-azido-4-(2H-tetrazol-5-yl)furazan with ammonia and guanylurea were also obtained and characterized.

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References

  1. Yin, P.; Shreeve, J. M. Adv. Heterocycl. Chem. 2017, 121, 89.

    Article  Google Scholar 

  2. Gao, H.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377.

    Article  CAS  Google Scholar 

  3. Ghule, V. D.; Sarangapani, R.; Jadhav, P. M.; Tewari, S. P. J. Mol. Model. 2011, 17, 1507.

    Article  CAS  Google Scholar 

  4. Wei, H.; He, C.; Zhang, J.; Shreeve, J. M. Angew. Chem., Int. Ed. 2015, 54, 9367.

    Article  CAS  Google Scholar 

  5. Ostrovskii, V. A.; Koldobskii, G. I.; Trifonov, R. E. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Amsterdam, 2008, Vol. 6, p. 257.

  6. Fershtat, L. L.; Makhova, N. N. Russ. Chem. Rev. 2016, 85, 1097. [Usp. Khim. 2016, 85, 1097.]

  7. Andrianov, V. G.; Eremeev, A. V. Chem. Heterocycl. Compd. 1994, 30, 608. [Khim. Geterotsikl. Soedin. 1994, 693.]

  8. Wang, R.; Guo, Y.; Zeng, Z.; Twamley, B.; Shreeve, J. M. Chem.–Eur. J. 2009, 15, 2625.

    Article  CAS  Google Scholar 

  9. Wang, B.; Zhang, G.; Huo, H.; Fan, Y.; Fan, X. Chin. J. Chem. 2011, 29, 919.

    Article  CAS  Google Scholar 

  10. Wang, J.-Y.; Liang, J.; Wu, B.-D.; An, C.-W. Main Group Chem. 2016, 15, 325.

    Article  CAS  Google Scholar 

  11. Huang, H.; Shi, Y.; Li, Y.; Liu, Y.; Yang, J. RSC Adv. 2016, 6, 64568.

    Article  CAS  Google Scholar 

  12. Godovikova, T.; Vorontsova, S.; Konyushkin, L.; Firgang, S.; Rakitin, O. Russ. Chem. Bull., Int. Ed. 2009, 58, 406. [Izv. Akad. Nauk, Ser. Khim. 2009, 400.]

  13. Li, H.; Yu, Q.; Wang, B.; Lai, W.; Ge, Z.; Li, Y.; Liu, N. Hanneng Cailiao 2013, 21, 821.

    CAS  Google Scholar 

  14. Leonard, P. W.; Chavez, D. E.; Pagoria, P. F.; Parrish, D. L. Propellants, Explos., Pyrotech. 2011, 36, 233.

    Article  CAS  Google Scholar 

  15. Liang, L.; Huang, H.; Wang, K.; Bian, C.; Song, J.; Ling, L.; Zhao, F.; Zhou, Z. J. Mater. Chem. 2012, 22, 21954.

    Article  CAS  Google Scholar 

  16. Li, H.; Wang, B.-Z.; Yu, Q.-Q.; Li, Y.-N.; Shang, Y. Hanneng Cailiao 2012, 20, 18.

    Google Scholar 

  17. Li, X.; Liu, X.; Zhang, S.; Wu, H.; Wang, B.; Yang, Q.; Wei, Q.; Xie, G.; Chen, S.; Gao, S. J. Chem. Eng. Data 2016, 61, 207.

    Article  CAS  Google Scholar 

  18. Li, X.-H.; Mei, Z.; Zhang, R.-Z.; Zhang, X.-Z. Mol. Phys. 2016, vol. 114, 23, 3437.

  19. Ilyushin, M. A.; Shugaley, I. V.; Tselinskii, I. V.; Garabadzhiu, A. V. Russ. J. Gen. Chem. 2013, 83, 2624. [Ekol. Khimiya 2012, 21, 154.]

  20. Ichikawa, T.; Kato, T.; Takenishi, T. J. Heterocycl. Chem. 1965, 2, 253.

    Article  CAS  Google Scholar 

  21. Stepanov, A. I.; Sannikov, V. S.; Dashko, D. V.; Astrat'yev, А. A. Izv. SPbGTI (TU) 2014, 25, 32.

    Google Scholar 

  22. Stepanova, E. V.; Stepanov, A. I.; Stepanov, V. A. In: Science Today: Proceedings of the International Scientific-practical Conference, Vologda, October 24, 2014 [in Russian]; Izdat. Dom Vologzhanin: Vologda, 2014, part 1, p. 14.

  23. Rozhkov, V. Yu.; Batog, L. V.; Struchkova, M. I. Russ. Chem. Bull., Int. Ed. 2005, 54, 1923. [Izv. Akad. Nauk, Ser. Khim. 2005, 1866.]

  24. Rakitin, O. A.; Zalesova, O. A.; Kulikov, A. S.; Makhova, N. N.; Godovikova, T. I.; Khmel'nitskii, L. I. Russ. Chem. Bull. 1993, 42, 1865. [Izv. Akad. Nauk, Ser. Khim. 1993, 1949.]

  25. Andrianov, V. G.; Eremeev, A. V. Chem. Heterocycl. Compd. 1984, 20, 937. [Khim. Geterotsikl. Soedin. 1984, 1155.]

  26. Andrianov, V. G.; Rozhkov, E. N.; Eremeev, A. V. Chem. Heterocycl. Compd. 1994, 30, 470. [Khim. Geterotsikl. Soedin. 1994, 534.]

  27. Stepanov, A. I.; Sannikov, V. S.; Dashko, D. V.; Roslyakov, A. G.; Astrat'ev, A. A.; Stepanova, E. V. Chem. Heterocycl. Compd. 2015, 51, 350. [Khim. Geterotsikl. Soedin. 2015, 51, 350.]

  28. Li, H.-Z.; Huang, M.; Li, J.-S.; Cheng, B.-B.; Zhou, X.-Q. Hecheng Huaxue 2007, 15, 710.

    CAS  Google Scholar 

  29. Zhou, Y.; Wang, B.; Zhou, C.; Li, J.; Chen, Z.; Lian, P.; Zhang, Z. Youji Huaxue 2010, 30, 1044.

    CAS  Google Scholar 

  30. Sheremetev, A. B.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu.; Antipin, M. Yu. Eur. J. Org. Chem. 2012, 11, 2266.

    Article  Google Scholar 

  31. Sheremetev, A. B.; Lyalin, B. V.; Kozeev, A. M.; Palysaeva, N. V.; Struchkova, M. I.; Suponitsky, K. Yu. RSC Adv. 2015, 5, 37617.

    Article  CAS  Google Scholar 

  32. Allen, F. H.; Kennard, O.; Watson, D. V.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.

  33. Khmelnitskii, L. I.; Novikov, S. S.; Godovikova, T. I. Chemistry of Furoxans: Structure and Synthesis [in Russian]; Nauka: Moscow, 1996, p. 43.

    Google Scholar 

  34. Fershtat, L. L.; Epishina, M. A.; Kulikov, A. S.; Ovchinnikov, I. V.; Ananyev, I. V.; Makhova, N. N. Tetrahedron 2015, 71, 6764.

    Article  CAS  Google Scholar 

  35. Shao, Y.; Zhu, W.; Xiao, H. J. Mol. Graphics Modell. 2013, 40, 54.

    Article  CAS  Google Scholar 

  36. Fizika vzryva [in Russian]; Orlenko, L. P., Ed.; Fizmatlit: Moscow, 2002, 3rd ed., Vol. 1, p. 204.

  37. Altomare, A.; Cascarno, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C. J. Appl. Crystallogr. 1993, 26, 343.

    Article  Google Scholar 

  38. Sheldrick, G. M. SHELXL 97; University of Göttingen, 1998.

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Authors and Affiliations

  1. Special Engineering and Design Bureau “Technolog”, 33-А Sovetsky Ave., Saint Petersburg, 192076, Russia

    Andrei I. Stepanov, Vladimir S. Sannikov, Dmitry V. Dashko, Aleksey G. Roslyakov & Alexander A. Astrat’yev

  2. Russian State Hydrometeorological University, 98 Malookhtinsky Ave., Saint Petersburg, 195196, Russia

    Elena V. Stepanova

  3. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Akademika Semenova Ave., Chernogolovka, 142432, Russia

    Zainutdin G. Aliev, Tel’man K. Goncharov & Sergei M. Aldoshin

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  1. Andrei I. Stepanov
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  2. Vladimir S. Sannikov
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  3. Dmitry V. Dashko
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Correspondence to Andrei I. Stepanov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 779–785

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Stepanov, A.I., Sannikov, V.S., Dashko, D.V. et al. Synthesis and properties of 3-azido-4-(2H-tetrazol-5-yl)furazan. Chem Heterocycl Comp 53, 779–785 (2017). https://doi.org/10.1007/s10593-017-2123-8

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