Skip to main content
Log in

2-Benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and Its Analogs in Aza-Michael Reaction

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

Abstract

2-Benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and its analogs have been introduced in the aza-Michael reaction with hydrazine derivatives. Novel polysubstituted nitrosulfolenes have been obtained; their structures have been confirmed using 1Н NMR and IR spectroscopy as well as X-ray diffraction analysis.

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

Access this article

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. Brant, M.G. and Wulff, J.E., Synthesis, 2016, vol. 48, p. 1. doi 10.1055/s-0035-1560351

    CAS  Google Scholar 

  2. Krautler, B., Sheehan, C.S., and Rieder, A., Helv. Chim. Acta, 2000, vol. 83, p. 583. doi 10.1002/(SICI)1522-2675(20000315)83:3< 583::AID-HLCA583>3.0.CO;2-A

    Article  CAS  Google Scholar 

  3. Subramanian, T., Meenakshi, S., Dange, S.Y., and Bhat, S.V., Synth. Commun., 1997, vol. 27, p. 2557. doi 10.1080/00397919708004123

    Article  CAS  Google Scholar 

  4. Brant, M.G. and Wulff, J.E., Org. Lett., 2012, vol. 14, p. 5876. doi 10.1021/ol3027939

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Patil, S.T., Zhang, L., Martenyi, F., Lowe, S.L., Jackson, K., A., Andreev, B.V., Avedisova, A.S., Bardenstein, L.M., Gurovich, I.Y., Morozova, M.A., Mosolov, S.N., Neznanov, N.G., Reznik, A.M., Smulevich, A.B., Tochilov, V.A., Johnson, B.G., Monn, J.A., and Schoepp, D.D., Nat. Med., 2007, vol. 13, p. 1102. doi 10.1038/nm1632

    Article  CAS  PubMed  Google Scholar 

  6. Oh, K., Org. Lett., 2007, vol. 9, p. 2973. doi 10.1021/ol0710663

    Article  CAS  PubMed  Google Scholar 

  7. Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes. Conjugated nitro Compounds, London: John Wiley and Sons, 1994.

    Google Scholar 

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

    Google Scholar 

  9. 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 

  10. Lapshina, L.V., Serebryannikova, A.V., Efremova, I.E., Perkhunova, A.D., Bortnikov, S.V., Be-restovitskaya, V.M., Russ. J. Gen. Chem., 2014, vol. 84, no. 8, p. 1519. doi 10.1134/S1070363214080131

    Article  CAS  Google Scholar 

  11. 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 

  12. 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 10.1134/S1070363216030191

    Article  CAS  Google Scholar 

  13. Berestovitskaya, V.M., Efremova, I.E., Serebryannikova, A.V., Lapshina, L.V., and Gurzhiy, V.V., Chem. Heterocycl. Compd., 2018, vol. 54, no. 1, p. 76. doi 10.1007/s10593-018-2233-y

    Article  CAS  Google Scholar 

  14. Strauss, L.H., Abzianidze, V.V., Berestovitskaya, V.M., and Efremova, I.E., Acta Crystallogr. (C), 2003, vol. 59, p. o177. doi 10.1107/S0108270103000842

    Google Scholar 

  15. Sheldrick, G.M,. SADABS, University of Goettingen, Germany, 2007.

    Google Scholar 

  16. Sheldrick, G.M., Acta Crystallogr. (C), 2015, vol. 71, p. 3. doi 10.1107/S2053229614024218

    Google Scholar 

  17. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. doi 10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  18. Spek, A.L., Acta Crystallogr. (C), 2015, vol. 71, p. 9. doi 10.1107/S2053229614024929

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. E. Efremova.

Additional information

Original Russian Text © A.V. Serebryannikova, L.V. Lapshina, I.E. Efremova, V.V. Gurzhiy, A.E. Ryabinin, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 8, pp. 1291–1296.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Serebryannikova, A.V., Lapshina, L.V., Efremova, I.E. et al. 2-Benzylidene-3-methyl-4-nitro-3-thiolene-1,1-dioxide and Its Analogs in Aza-Michael Reaction. Russ J Gen Chem 88, 1612–1617 (2018). https://doi.org/10.1134/S1070363218080108

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218080108

Keywords

Navigation