Skip to main content
Log in

Synthesis of 6-sulfamoylsaccharin and study of its reactivity in alkylation reactions

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

An improved method for the preparation of 6-sulfamoylsaccharin (3-oxo-2,3-dihydro-1,2-benzo-thiazole-6-sulfonamide 1,1-dioxide) has been developed and studies of its possible direct alkylation have been carried out. It was shown that alkylation occurs regioselectively at the isothiazoline ring nitrogen atom.

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. R. Okachi, H. Niino, K. Kitaura, K. Mineura, Y. Nakamizo, Y. Murayama, T. Ono, and A. Nakamizo, J. Med. Chem., 28, 1772 (1985).

    Article  CAS  Google Scholar 

  2. D. Goukassian, S. M. Sanz-González, I. Pérez-Roger, J. F. de Mora, J. Ureña, and V. Andrés, Br. J. Pharmacol., 132, 1597 (2001).

    Article  CAS  Google Scholar 

  3. A. L. Vaccarino, D. Paul, P. K. Mukherjee, E. B. Rodríguez de Turco, V. L. Marcheselli, L. Xu, M. L. Trudell, J. M. Minguez, M. P. Matía, C. Sunkel, J. Alvarez-Builla, and N. G. Bazan, Bioorg. Med. Chem., 15, 2206 (2007).

    Article  CAS  Google Scholar 

  4. M. Rami, J.-Y. Winum, A. Innocenti, J.-L. Montero, A. Scozzafava, and C. T. Supuran, Bioorg. Med. Chem. Lett., 18, 836 (2008).

    Article  CAS  Google Scholar 

  5. C. T. Supuran, A. Scozzafava, and J. Conway, Carbonic Anhydrase: Its Inhibitors and Activators, CRC Press, Boca Raton, New York, London (2004).

    Google Scholar 

  6. A. A. Spryskov and T. I. Yakovleva, Zh. Obshch. Khim., 25, 783 (1955).

    CAS  Google Scholar 

  7. E. Yuriev, D. C. M. Kong, and M. N. Iskander, Eur. J. Med. Chem., 39, 835 (2004).

    Article  CAS  Google Scholar 

  8. A. V. Tarasov, P. O. Yablonskii, and Yu. A. Moskvichev, Khim. Geterotsikl. Soedin., 126 (2003). [Chem. Heterocycl. Comp., 39, 119 (2003)].

    Google Scholar 

  9. H. Kamogawa, S. Yamamoto, and M. Nanasawa, Bull. Chem. Soc. Jpn., 55, 3824 (1982).

    Article  CAS  Google Scholar 

  10. L. Xu, H. Shu, Y. Liu, S. Zhang, and M. L. Trudell, Tetrahedron, 62, 7902 (2006).

    Article  CAS  Google Scholar 

  11. V. N. Voshchula, S. V. Tolkunov, M. Yu. Zubritskii, and V. I. Dulenko, Khim. Geterotsikl. Soedin., 1414 (1988). [Chem. Heterocycl. Comp., 24, 1175 (1988)].

    Google Scholar 

  12. Z. Jakopin and M. S. Dolenc, Synth. Commun., 40, 2464 (2010).

    Article  CAS  Google Scholar 

  13. G. H. Hamor, J. Pharm. Sci., 51, 1109 (1962).

    Article  CAS  Google Scholar 

Download references

This work was carried out with the financial support of the European Social Fund (No. 2009/0203/1DP/1.1.1.2.0/APIA/VIAA/023).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R. Žalubovskis.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1865-1868, December, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ivanova, E.M., Simin, E.Y., Vozny, I.V. et al. Synthesis of 6-sulfamoylsaccharin and study of its reactivity in alkylation reactions. Chem Heterocycl Comp 47, 1561–1564 (2012). https://doi.org/10.1007/s10593-012-0948-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-0948-8

Keywords

Navigation