Russian Journal of Organic Chemistry

, Volume 53, Issue 11, pp 1717–1725 | Cite as

Synthesis of new N-polysubstituted oxaazaisowurtzitanes by acid-catalyzed condensation of sulfonamides with glyoxal

  • A. E. Paromov
  • S. V. Sysolyatin


By application of acid-catalyzed condensation of propane-2-, benzene- and methanesulfonamides with glyoxal a series of new derivatives of oxaazaisowurtzitanes were obtained, in particular, new heterocyclic systems: 2,4,6,8,12-pentaoxa-10-aza- and 2,4,8,12-tetraoxa-6,10-diazatetracyclo[,11.05,9]-dodecanes.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Kleinschmidt, E. and Wanninger, P., FRG Patent no. 4324739, 1994.Google Scholar
  2. 2.
    Clement, D., Koch, E.-C., Rudolf, K., Eigenmann, B., 10th Seminar “New Trends in Research of Energetic Materials”, Pardubice, Czech Republic, 25–27 April, 2008, p. 128.Google Scholar
  3. 3.
    Radacsi, N., Bouma, R.H.B., Krabbendamla Haye, E.L.M., ter Horst, J.H., Stankiewicz, A.I., and van der Heijden, A.E.D.M., Propellants, Explos., Pyrotech., 2013, vol. 38, p. 761.CrossRefGoogle Scholar
  4. 4.
    Risse, B., Schell, F., and Spitzer, D., Propellants, Explos., Pyrotech., 2014, vol. 39, p. 391.CrossRefGoogle Scholar
  5. 5.
    Doherty, R.M. and Watt, D.S., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 4.CrossRefGoogle Scholar
  6. 6.
    Borne, L., Mory, J., and Schlesser, F., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 37.CrossRefGoogle Scholar
  7. 7.
    Sakovich, G.V., Sysolyatin, S.V., Kozyrev, N.V., Makarovets, N.A., RF Patent no. 2252925, 2003.Google Scholar
  8. 8.
    Nielsen, A.T., US Patent no. 5693794, 1997.Google Scholar
  9. 9.
    Nielsen, A.T., Chafin, A.P., Christian, S.L., Moore, D.W., Nadler, M.P., Nissan, R.A., and Vanderah, D.J., Tetrahedron, 1998, vol. 54, p. 11793. doi 10.1016/S0040-4020(98)83040-8CrossRefGoogle Scholar
  10. 10.
    Piacenza, G., Blaive, B., Gallo, R., and Jacob, G., 28th International Annual Conference of ICT, Combustion and Detonation, Karlsruhe, Germany, 24–27 June, 1997, p. 123/1.Google Scholar
  11. 11.
    Walsh, M.E., Jenkins, T.F., and Thorne, P.G., J. Energ. Mater., 1995, vol. 13, p. 357.CrossRefGoogle Scholar
  12. 12.
    Bircher, H.R., Maeder, P., and Mathieu, J., 29th Proceedings of International Annual Conference of ICT, Karlsruhe, Germany, 1998, p. 94/1.Google Scholar
  13. 13.
    Stepanov, R.S. and Kruglyakova, L.A., Russ. J. Gen. Chem., 2010, vol. 80, p. 316. doi 10.1134/S1070363210020210CrossRefGoogle Scholar
  14. 14.
    Gatilov, Yu.V., Rybalova, T.V., Efimov, O.A., and Lobanova, A.A., J. Struct. Chem., 2005, vol. 46, p. 566. doi 10.1007/s10947-006-0141-yCrossRefGoogle Scholar
  15. 15.
    Vagenknecht, J., Marecek, P., and Trzcinski, W.A., J. Energ. Mater., 2002, vol. 20, p. 245.CrossRefGoogle Scholar
  16. 16.
    Koch, E.-C., Prop. Explos. Pyrotech., 2015, vol. 40, p. 374.CrossRefGoogle Scholar
  17. 17.
    Sysolyatin, S.V., Sakovich, G.V., Chernikova, Y.T., Surmachev, V.N., and Lobanova, A.A., 37th International Annual Conference of ICT, Karlsruhe, Germany, 27–30 June, 2006, p. 141.Google Scholar
  18. 18.
    Ramakrishnan, V.T., Vedachalam, M., and Boyer, J.H., Heterocycles, 1990, vol. 31, p. 479.CrossRefGoogle Scholar
  19. 19.
    Highsmith, T.K., Edwards, W.W., and Wardle, R.B., US Patent no. 5498711, 1996.Google Scholar
  20. 20.
    Ghaderia, H., Zolfigol, M.A., Bayat, Y., Zareia, M., and Noroozizadeha, E., Synlett., 2016, vol. 27, p. 2246.CrossRefGoogle Scholar
  21. 21.
    Sysolyatin, S.V., Lobanova, A.A., and Chernikova, Y.T., International Conference “Modern Problems of Organic Chemistry”, Novosibirsk, 27–30 September, 2001, p. 104.Google Scholar
  22. 22.
    Sysolyatin, S.V., Surmachev, V.N., Lobanova, A.A., Chernikova, Y.T., and Sakovich, G.V., 5th International Conference & Exhibit “High Energy Materials”, DRDL, Hyderabad, 23–25 November, 2005, p. 101.Google Scholar
  23. 23.
    Kerscher, T., Klapotke, T., Krumm, B., Polborn, K., and Scherr, M., J. Fluor. Chem., 2006, vol. 127, p. 1030.CrossRefGoogle Scholar
  24. 24.
    Kalashnikov, A.I., Sysolyatin, S.V., and Shein, N.V., Polzynovskii Vestn., 2013, p. 42.Google Scholar
  25. 25.
    Sysolyatin, S.V., Kalashnikov, A.I., Lobanova, A.A., Chernikova, Yu.T., and Kadulin, V.V., RF Patent no. 2355693, 2009.Google Scholar
  26. 26.
    Paromov, A.E., Sysolyatin, S.V., and Gatilov, Y.V., J. Energ. Mater., 2017, vol. 35, p. 363.CrossRefGoogle Scholar
  27. 27.
    Paromov, A.E., Abstracts of Papers, V Vserossiiskaya nauchno-tekhnicheskaya konferentsiya molodykh uchonykh, “Perspektivy sozdaniya i primeneniya kondensirovannykh vysokoenergeticheskikh materialov” (Vth All-Russian Scientific Conf. of Young Scientists “Perspectives of Creation and Application of Condensed High-energy Materials”), IPKhET SO RAN, 11-12 September, 2014, Biisk: Izd. Altais. Gos. Tekhn. Univer., p. 35.Google Scholar
  28. 28.
    Klages, F., Jung, H.A., and Hegenberg, P., Chem. Ber., 1966, vol. 99, p. 1701.CrossRefGoogle Scholar
  29. 29.
    Yang, K., Ke, M., Lin, Y., and Song, Q., Green Chem., 2015, vol. 17, p. 1395.CrossRefGoogle Scholar
  30. 30.
    Zhou, Y., Li, L., Webber, S.E., Dragovich, P., Murphy, D.E., Tran, C.V., Zhao, J., and Ruebsam, F., WO Appl. no. 2008082725, 2008.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  1. 1.Institute for Problems of Chemical and Energetic TechnologiesSiberian Branch of the Russian Academy of SciencesBiyskRussia

Personalised recommendations