Log in

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

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

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[5.5.0.03,11.05,9]-dodecanes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Kleinschmidt, E. and Wanninger, P., FRG Patent no. 4324739, 1994.

    Google Scholar 

  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. 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.

    Article  CAS  Google Scholar 

  4. Risse, B., Schell, F., and Spitzer, D., Propellants, Explos., Pyrotech., 2014, vol. 39, p. 391.

    Article  Google Scholar 

  5. Doherty, R.M. and Watt, D.S., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 4.

    Article  CAS  Google Scholar 

  6. Borne, L., Mory, J., and Schlesser, F., Propellants, Explos., Pyrotech., 2008, vol. 33, p. 37.

    Article  CAS  Google Scholar 

  7. Sakovich, G.V., Sysolyatin, S.V., Kozyrev, N.V., Makarovets, N.A., RF Patent no. 2252925, 2003.

    Google Scholar 

  8. Nielsen, A.T., US Patent no. 5693794, 1997.

    Google Scholar 

  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)83040-8

    Article  CAS  Google Scholar 

  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. Walsh, M.E., Jenkins, T.F., and Thorne, P.G., J. Energ. Mater., 1995, vol. 13, p. 357.

    Article  CAS  Google Scholar 

  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. Stepanov, R.S. and Kruglyakova, L.A., Russ. J. Gen. Chem., 2010, vol. 80, p. 316. doi 10.1134/S1070363210020210

    Article  CAS  Google Scholar 

  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-y

    Article  CAS  Google Scholar 

  15. Vagenknecht, J., Marecek, P., and Trzcinski, W.A., J. Energ. Mater., 2002, vol. 20, p. 245.

    Article  CAS  Google Scholar 

  16. Koch, E.-C., Prop. Explos. Pyrotech., 2015, vol. 40, p. 374.

    Article  CAS  Google Scholar 

  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. Ramakrishnan, V.T., Vedachalam, M., and Boyer, J.H., Heterocycles, 1990, vol. 31, p. 479.

    Article  CAS  Google Scholar 

  19. Highsmith, T.K., Edwards, W.W., and Wardle, R.B., US Patent no. 5498711, 1996.

    Google Scholar 

  20. Ghaderia, H., Zolfigol, M.A., Bayat, Y., Zareia, M., and Noroozizadeha, E., Synlett., 2016, vol. 27, p. 2246.

    Article  Google Scholar 

  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. 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. Kerscher, T., Klapotke, T., Krumm, B., Polborn, K., and Scherr, M., J. Fluor. Chem., 2006, vol. 127, p. 1030.

    Article  CAS  Google Scholar 

  24. Kalashnikov, A.I., Sysolyatin, S.V., and Shein, N.V., Polzynovskii Vestn., 2013, p. 42.

    Google Scholar 

  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. Paromov, A.E., Sysolyatin, S.V., and Gatilov, Y.V., J. Energ. Mater., 2017, vol. 35, p. 363.

    Article  CAS  Google Scholar 

  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. Klages, F., Jung, H.A., and Hegenberg, P., Chem. Ber., 1966, vol. 99, p. 1701.

    Article  Google Scholar 

  29. Yang, K., Ke, M., Lin, Y., and Song, Q., Green Chem., 2015, vol. 17, p. 1395.

    Article  CAS  Google Scholar 

  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 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. V. Sysolyatin.

Additional information

Original Russian Text © A.E. Paromov, S.V. Sysolyatin, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 11, pp. 1680–1688.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Paromov, A.E., Sysolyatin, S.V. Synthesis of new N-polysubstituted oxaazaisowurtzitanes by acid-catalyzed condensation of sulfonamides with glyoxal. Russ J Org Chem 53, 1717–1725 (2017). https://doi.org/10.1134/S1070428017110197

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428017110197

Navigation