Skip to main content
SpringerLink
Log in

Synthesis of 1,3-benzothiazol-2(3H)-ones with a carbamate function at the C-6 atom

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A new method has been developed for the synthesis of 1,3-benzothiazol-2(3H)-ones with carbamate function based on the adducts of the 1,4-addition of thioacetic acid to 2-R-N,N'-dimethoxycarbonyl-1,4-benzoquinone diimines. Refluxing the 2-thioacetyl-substituted dicarbamates in ethanol in the presence of hydrochloric acid gave 1,3-benzothiazol-2(3H)-ones with methoxycarbonylamine group at the C-6 atom. Modifications of the obtained compounds were performed.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J. Dündar, B. Çakir, E. Küpeli, and M. F. Şahin, Turk. J. Pharm. Sci., 3, 51 (2006).

    Google Scholar 

  2. H. T. Fife, J. E. C. Hutchins, and M. S. Wang, J. Am. Chem. Soc., 97, 5878 (1975).

    Article  CAS  Google Scholar 

  3. R. Shridhar and P. T. Perumal, Synth. Commun., 34, 735 (2004).

    Article  Google Scholar 

  4. S. Yous, V. Wallez, M. Belloir, D. H. Caignard, C. R. McCurdy, and J. H. Poupaert, Med. Chem. Res., 14, 158 (2005).

    Article  CAS  Google Scholar 

  5. A. V. Velikorodov, A. K. Kuanchalieva, E. A. Melent’eva, Zh. Org. Khim, 47, 1353 (2011).

    Google Scholar 

  6. H. Aichaoui, F. Guenadil, C. N. Kapanda, D. M. Lambert, C. R. McCurdy, and J. H. Poupaert, Med. Chem. Res., 18, 467 (2009).

    Article  CAS  Google Scholar 

  7. H. Ucar, K. Van derpoorten, S. Cacciaguerra, S. Spampinato, J. P. Stables, P. Depovere, M. Isa, B. Masereel, J. Delarge, and J. H. Poupaert, J. Med. Chem., 41, 1138 (1998).

    Article  CAS  Google Scholar 

  8. Y. Ivanova, O. Petrov, M, Gerova, and G. Momekov, C. R. Acad. Bulg. Sci., 60, 641 (2007).

    CAS  Google Scholar 

  9. A. R. Katritzky, D. Fedoseyenko, P. P. Mohapatra, and F. J. Steel, Synthesis, 777 (2008).

  10. R. Adams and W. Reifschneider, Bull. Soc. Chim. Fr., 23 (1958).

  11. S. Fujita, J. Synth. Org. Chem. Jpn., 43, 153 (1985).

    Article  CAS  Google Scholar 

  12. R. Adams and R. S. Colgrove, J. Am. Chem. Soc., 76, 3584 (1954).

    Article  CAS  Google Scholar 

  13. T. N. Maksimova and A. V. Velikorodov, Zh. Org. Khim. 22, 1092 (1986).

    CAS  Google Scholar 

  14. A. V. Velikorodov, T. N. Maksimova, A. G. Tyrkov, and V. B. Mochalin, Izv.Vuzov. Khimiya i Khim. Tekhnologiya, 34, 30 (1991).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Astrakhan State University, 1 Shaumyan Sq., Astrakhan, 414000, Russia

    A. V. Velikorodov, A. K. Kuanchalieva & V. A. Ionova

Authors
  1. A. V. Velikorodov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. K. Kuanchalieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Ionova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Velikorodov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1808-1812, November, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Velikorodov, A.V., Kuanchalieva, A.K. & Ionova, V.A. Synthesis of 1,3-benzothiazol-2(3H)-ones with a carbamate function at the C-6 atom. Chem Heterocycl Comp 48, 1691–1695 (2013). https://doi.org/10.1007/s10593-013-1194-4

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1194-4

Keywords

Search

Navigation