Russian Journal of General Chemistry

, Volume 86, Issue 3, pp 622–628 | Cite as

Synthesis of new bicyclic compounds containing fused sulfolane and pyrazolidine rings

  • I. E. Efremova
  • A. V. Serebryannikova
  • L. V. Lapshina
  • V. V. Gurzhiy
  • V. M. Berestovitskaya
Article

Abstract

3-Aryl-6а-methyl-6-nitro-1-carbamoylhexahydrothieno[2,3-d]pyrazole-4,4-dioxides, novel original bicyclic species consisting of fused pyrazolidine and sulfolane rings, and 1,4-adducts were obtained by reacting 2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and its derivatives with semicarbazide.

Keywords

sulfolane pyrazolidine bicyclic compounds nitrosulfodienes semicarbazide nucleophilic addition heterocyclization 

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References

  1. 1.
    Brant, M.G. and Wulff, J.E., Org. Lett., 2012, vol. 14, p. 5876. DOI: 10.1021/ol3027939.CrossRefGoogle Scholar
  2. 2.
    Eid, A.A., Koubeissi, A., Bou-Mjahed, R., Al Khalil, N., Farah, M., Maalouf, R., Nasser, N., and Bouhadir, K.H., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 174. DOI: 10.1016/j.bmcl.2012.10.122.CrossRefGoogle Scholar
  3. 3.
    Kiriazis, A., af Gennäs, G.B., Talman, V., Ekokoski, E., Ruotsalainen, T., Kylänlahti, I., Ruffer, T., Wissel, G., Xhaard, H., Lang, H., Tuominen, R.K., and Yli-Kauhaluoma, J., Tetrahedron, 2011, vol. 67, p. 8665. DOI: 10.1016/j.tet.2011.09.044.CrossRefGoogle Scholar
  4. 4.
    Li, B., Buzon, R.A., and Hritzko, B., Synlett, 2012, vol. 23, p. 131. DOI: 10.1055/s-0031-1290089.CrossRefGoogle Scholar
  5. 5.
    Oh, K., Org. Lett., 2007, vol. 9, p. 2973. DOI: 10.1021/ol0710663.CrossRefGoogle Scholar
  6. 6.
    Tolstikov, G.A., Shul’ts, E.E., Vafina, G.F., Spirikhin, L.V., Zh. Org. Khim., 1992, vol. 28, no. 2, p.190.Google Scholar
  7. 7.
    Waser, M., Moher, E.D., Borders, S.S.K., Hansen, M.M., Hoard, D.W., Laurila, M.E., LeTourneau, M.E., Miller, R.D., Phillips, M.L., Sullivan, K.A., Ward, J.A., Xie, C., Bye, C.A., Leitner, T., Herzog-Krimbacher, B., Kordian, M., and Mullner, M., Org. Proc. Res. Dev., 2011, vol. 15, p. 1266. DOI: 10.1021/op100325h.CrossRefGoogle Scholar
  8. 8.
    Zarovnaya, I.S., Zlenko, H.T., and Palchikov, V.A., Eur. Chem. Bull., 2014, vol. 3, p.543.Google Scholar
  9. 9.
    Wong, S.S.Y., Brant, M.G., Barr, C., Oliver, A.G., and Wulff, J.E., Beilstein J. Org. Chem., 2013, vol. 9, p. 1419. DOI: 10.3762/bjoc.9.159.CrossRefGoogle Scholar
  10. 10.
    Gore, P.M., Hancock, A.P., Hodgson, S.T., Procopiou, P.A., and Vile, S., WO Patent 2009021965 A3, 2009.Google Scholar
  11. 11.
    Berestovitskaya, V.M., Zh. Obshch. Khim., 2000, vol. 70, no. 9, p. 1512.Google Scholar
  12. 12.
    Berestovitskaya, V.M., Selivanova, M.V., Vakulenko, M.I., Efremova, I.E., and Berkova, G.A., Russ. J. Org. Chem., 2009, vol. 45, no. 12, p. 1814. DOI: 10.1134/S1070428009120100.CrossRefGoogle Scholar
  13. 13.
    Berestovitskaya, V.M., Efremova, I.E., Lapshina, L.V., Serebryannikova, A.V., Gurzhiy, V.V., and Abzianidze, V.V., Mendeleev Commun., 2015, vol. 25, p. 191. DOI: 10.1016/j.mencom.2015.05.010.CrossRefGoogle Scholar
  14. 14.
    Ziyaei-Halimehjani, A., Namboothiri, I.N.N., and Hooshmand, S.E., RSC Adv., 2014, vol. 4, p. 48022. DOI: 10.1039/C4RA08828J.CrossRefGoogle Scholar
  15. 15.
    Ziyaei-Halimehjani, A., Namboothiri, I.N.N., and Hooshmand, S.E., RSC Adv., 2014, vol. 4, p. 31261. DOI: 10.1039/C4RA04069D.CrossRefGoogle Scholar
  16. 16.
    Lapshina, L.V., Serebryannikova, A.V., Efremova, I.E., Perkhunova, A.D., Bortnikov, S.V., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2014, vol. 84, no. 8, p. 1519. DOI: 10.1134/S10703632140801.CrossRefGoogle Scholar
  17. 17.
    Berestovitskaya, V.M., Efremova, I.E., Trukhin, E.V., and Berkova, G.A., Zh. Org. Khim., 1993, vol. 29, no. 2, p.368.Google Scholar
  18. 18.
    Baldwin, J.E., J. Chem. Soc. Chem. Commun., 1976, p.734.Google Scholar
  19. 19.
    Argyle, C.S., Goadby, S.C., Mason, K.G., Reed, R.A., Smith, M.A., and Stern, E.S., J. Chem. Soc. (C), 1967, vol. 21, p. 2156.Google Scholar
  20. 20.
    Pretch, E., Bühlmann, P., and Affolter, C., Structure Determination of Organic Compounds: Tables of Spectral Data, Berlin: Springer, 2000.CrossRefGoogle Scholar
  21. 21.
    Spek, A.L., PLATON, A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands, 2005.Google Scholar
  22. 22.
    Sheldrick, G.M., SADABS, University of Göttingen, Göttingen, Germany, 2004.Google Scholar
  23. 23.
    Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. DOI: 10.1107/S0108767307043930.CrossRefGoogle Scholar
  24. 24.
    Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339. DOI: 10.1107/S0021889808042726.CrossRefGoogle Scholar
  25. 25.
    Vasil’eva, M.V., Berestovitskaya, V.M., Berkova, G.A., and Pozdnyakov, V.P., Zh. Org. Khim., 1986, vol. 22, p. 428.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • I. E. Efremova
    • 1
  • A. V. Serebryannikova
    • 1
  • L. V. Lapshina
    • 2
  • V. V. Gurzhiy
    • 3
  • V. M. Berestovitskaya
    • 1
  1. 1.Herzen State Pedagogical University of RussiaSt. PetersburgRussia
  2. 2.Kirov Military Medical AcademySt. PetersburgRussia
  3. 3.St. Petersburg State UniversitySt. PetersburgRussia

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