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Synthesis of new bicyclic compounds containing fused sulfolane and pyrazolidine rings

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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.

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References

  1. Brant, M.G. and Wulff, J.E., Org. Lett., 2012, vol. 14, p. 5876. DOI: 10.1021/ol3027939.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  4. Li, B., Buzon, R.A., and Hritzko, B., Synlett, 2012, vol. 23, p. 131. DOI: 10.1055/s-0031-1290089.

    Article  CAS  Google Scholar 

  5. Oh, K., Org. Lett., 2007, vol. 9, p. 2973. DOI: 10.1021/ol0710663.

    Article  CAS  Google Scholar 

  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. 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.

    Article  CAS  Google Scholar 

  8. Zarovnaya, I.S., Zlenko, H.T., and Palchikov, V.A., Eur. Chem. Bull., 2014, vol. 3, p.543.

    CAS  Google Scholar 

  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.

    Article  Google Scholar 

  10. Gore, P.M., Hancock, A.P., Hodgson, S.T., Procopiou, P.A., and Vile, S., WO Patent 2009021965 A3, 2009.

    Google Scholar 

  11. Berestovitskaya, V.M., Zh. Obshch. Khim., 2000, vol. 70, no. 9, p. 1512.

    Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  14. Ziyaei-Halimehjani, A., Namboothiri, I.N.N., and Hooshmand, S.E., RSC Adv., 2014, vol. 4, p. 48022. DOI: 10.1039/C4RA08828J.

    Article  Google Scholar 

  15. Ziyaei-Halimehjani, A., Namboothiri, I.N.N., and Hooshmand, S.E., RSC Adv., 2014, vol. 4, p. 31261. DOI: 10.1039/C4RA04069D.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  17. Berestovitskaya, V.M., Efremova, I.E., Trukhin, E.V., and Berkova, G.A., Zh. Org. Khim., 1993, vol. 29, no. 2, p.368.

    CAS  Google Scholar 

  18. Baldwin, J.E., J. Chem. Soc. Chem. Commun., 1976, p.734.

    Google Scholar 

  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. Pretch, E., Bühlmann, P., and Affolter, C., Structure Determination of Organic Compounds: Tables of Spectral Data, Berlin: Springer, 2000.

    Book  Google Scholar 

  21. Spek, A.L., PLATON, A Multipurpose Crystallographic Tool. Utrecht University, Utrecht, The Netherlands, 2005.

    Google Scholar 

  22. Sheldrick, G.M., SADABS, University of Göttingen, Göttingen, Germany, 2004.

    Google Scholar 

  23. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. DOI: 10.1107/S0108767307043930.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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 

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Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, nab. reki Moiki 48, St. Petersburg, 191186, Russia

    I. E. Efremova, A. V. Serebryannikova & V. M. Berestovitskaya

  2. Kirov Military Medical Academy, St. Petersburg, Russia

    L. V. Lapshina

  3. St. Petersburg State University, St. Petersburg, Russia

    V. V. Gurzhiy

Authors
  1. I. E. Efremova
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  2. A. V. Serebryannikova
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  3. L. V. Lapshina
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  4. V. V. Gurzhiy
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  5. V. M. Berestovitskaya
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Corresponding author

Correspondence to I. E. Efremova.

Additional information

Original Russian Text © I.E. Efremova, A.V. Serebryannikova, L.V. Lapshina, V.V. Gurzhiy, V.M. Berestovitskaya, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 3, pp. 481–488.

To the 100th Anniversary of A.N. Pudovik

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Efremova, I.E., Serebryannikova, A.V., Lapshina, L.V. et al. Synthesis of new bicyclic compounds containing fused sulfolane and pyrazolidine rings. Russ J Gen Chem 86, 622–628 (2016). https://doi.org/10.1134/S1070363216030191

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  • DOI: https://doi.org/10.1134/S1070363216030191

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