Synthesis of New Sulfolanopyrazolidines

Abstract

3-Aryl-6a-methyl-6-nitrohexahydrothieno[2,3-d]pyrazole-4,4-dioxides, new representatives of original bicyclic structures combining fused pyrazolidine and sulfolane rings in a molecule, were obtained through the reactions of 2-benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and its substituted analogues with hydrazine. Structure of the bicycles obtained was established on the basis of a comprehensive analysis of IR, 1H, 13C{1H}, 1H-13C HMQC, 1H-13C HMBC spectroscopy data, and quantum-chemical calculations.

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

References

  1. 1.

    Tufariello, J.J., in Nitrones in 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed., New York: Wiley, 1984, vol. 2, p. 83.

  2. 2.

    Confalone, P.N. and Huie, E.M., Org. React., 1988, vol. 36, p. 1. doi https://doi.org/10.1002/0471264180.or036.01

    CAS  Google Scholar 

  3. 3.

    Asaoka, M., Mukuta, T., and Takei, H., Tetrahedron Zett., 1981, vol. 22, no. 8, p. 735. doi https://doi.org/10.1016/0040-4039(81)80137-2

    Article  CAS  Google Scholar 

  4. 4.

    Padwa, A., Koehler, K.F., and Rodriguez, A., J. Org. Chem., 1984, vol. 49, no. 2, p. 282. doi https://doi.org/10.1021/jo00176a013

    Article  CAS  Google Scholar 

  5. 5.

    Chuang, T.-H. and Sharpless, K.B., Helv. Chim. Acta, 2000, vol. 83, no. 8, p. 1734. doi <1734::AID-HLCA1734>3.0.CO;2-E

    Article  CAS  Google Scholar 

  6. 6.

    Pietrusiewicz, K.M., Hozody, W., Koprowski, M., Cicchi, S., Goti, A., and Brandi, A., Phosphorus, Sulfur, Silicon, Relat. Elem., 1999, vol. 144, p. 389. doi https://doi.org/10.1080/10426509908546263

    Article  Google Scholar 

  7. 7.

    Berestovitskaya, V.M., Zh. Obshch. Khim., 2000, vol. 70, p. 1512.

    Google Scholar 

  8. 8.

    Efremova, I.E., Serebryannikova, A.V., Lapshina, L.V., Gurzhiy, V.V., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2016, vol. 86, no. 3, p. 622. doi https://doi.org/10.1134/S1070363216030191

    Article  CAS  Google Scholar 

  9. 9.

    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 https://doi.org/10.1016/j.mencom.2015.05.010

    Article  CAS  Google Scholar 

  10. 10.

    Rulev, A.Yu., Russ. Chem. Rev., 2011, vol. 80, no. 3, p. 197. doi https://doi.org/10.1070/RC2011v080n03ABEH004162

    Article  CAS  Google Scholar 

  11. 11.

    Gorobets, E.V., Miftakhov, M.S., and Valeev, F.A., Russ. Chem. Rev., 2000, vol. 69, no. 12, p. 1001. doi https://doi.org/10.1070/RC2000v069n12ABEH000614

    Article  CAS  Google Scholar 

  12. 12.

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

  13. 13.

    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 

  14. 14.

    Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision D01, Gaussian Inc., Wallingford CT, 2013.

    Google Scholar 

  15. 15.

    Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648. doi https://doi.org/10.1063/1.464913

    Article  CAS  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to I. E. Efremova.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Efremova, I.E., Serebryannikova, A.V., Belyakov, A.V. et al. Synthesis of New Sulfolanopyrazolidines. Russ J Gen Chem 89, 536–539 (2019). https://doi.org/10.1134/S1070363219030277

Download citation

Keywords

  • sulfolanes
  • pyrazolidines
  • bicycles
  • hydrazine
  • nucleophilic addition
  • aza-Michael reaction