Skip to main content
SpringerLink
Log in

Brønsted acidic ionic liquids catalyzed the preparation of 13-aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones and 3,4-dihydro-1H-benzo[b]xanthene-1,6,11(2H,12H)-triones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

An environmentally green method for the synthesis of 13-aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraone and 3,4-dihydro-1H-benzo[b]xanthene-1,6,11(2H,12H)-trione derivatives using Brønsted acidic ionic liquids, 3-methyl-1-sulfonic acid imidazolium chloride, 1-H-3-methyl-imidazolium hydrogensulfate, triethylamine-bonded sulfonic acid, and triethylammonium hydrogensulfate as reusable catalysts under thermal solvent-free conditions is described.

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

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. W. Zhang, B.W. Cue, Green Techniques for Organic Synthesis and Medicinal Chemistry (Wiley, Chichester, 2012)

    Book  Google Scholar 

  2. A.M. Inamuddin, Green Solvents I: Properties and Applications in Chemistry (Springer, London, 2012)

    Google Scholar 

  3. A.M. Inamuddin, Green Solvents II: Properties and Applications in Chemistry (Springer, London, 2012)

    Google Scholar 

  4. B.S. Siddiqui, M.N. Kardar, T. Ali, S. Khan, Helv. Chim. Acta 86, 2164 (2003)

    Article  CAS  Google Scholar 

  5. C. Wright, G.V. Ullas, J. Label. Compd. Radiopharm. 45, 1265 (2002)

    Article  CAS  Google Scholar 

  6. R.H. Thomson, Naturally occurring quinines, 4th edn. (Chapman & Hall, London, 1997)

    Google Scholar 

  7. T. Hideo, J. Teruomi, Jpn. Patent 56,005,480 1981

  8. R.W. Lamberk, J.A. Martin, J.H. Merrett, K.E.B. Parkes, G.J. Thomas, PCT Int. Appl. WO9,706,178, 1997

    Google Scholar 

  9. J.P. Poupelin, G. Saint-Rut, O. Fussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lakroix, Eur. J. Med. Chem. 13, 67 (1978)

    CAS  Google Scholar 

  10. R.-M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochim. Pol. 45, 833 (1998)

    CAS  Google Scholar 

  11. A. Banerjee, A.K. Mukherjee, Stain Technol. 56, 83 (1981)

    CAS  Google Scholar 

  12. C.G. Knight, T. Stephenes, Biochem. J. 258, 683 (1989)

    CAS  Google Scholar 

  13. J. Peters, J. Grotemeyer, Rapid Commun Mass Spectrom. 25, 1169 (2011)

    Article  CAS  Google Scholar 

  14. Z. Noroozi Tisseh, S.C. Azimi, P. Mirzaei, A. Bazgir, Dye. Pigm. 79, 273 (2008)

    Article  Google Scholar 

  15. A. Bazgir, Z. Noroozi Tisseh, P. Mirzaei, Tetrahedron Lett. 49, 5165 (2008)

    Article  CAS  Google Scholar 

  16. H.R. Shaterian, M. Ranjbar, K. Azizi, J. Mol. Liq. 162, 95 (2011)

    Article  CAS  Google Scholar 

  17. H.R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 158, 145 (2011)

    Article  CAS  Google Scholar 

  18. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran Chem. 7, 646 (2010)

    Article  CAS  Google Scholar 

  19. A.R. Hajipour, L. Khazdooz, A.E. Ruoho, Catal. Commun. 9, 89 (2008)

    Article  CAS  Google Scholar 

  20. A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq. 167, 69 (2012)

    Article  CAS  Google Scholar 

  21. J. Weng, C. Wang, H. Li, Y. Wang, Green Chem. 8, 96 (2006)

    Article  CAS  Google Scholar 

  22. M. Mohammadpour-Amini, Y. Fazaeli, Z. Yassaee, S. Feizi, A. Bazgir, Open Catal. J. 2, 40 (2009)

    Article  Google Scholar 

  23. M. Dabiri, Z. Noroozi Tisseh, A. Bazgir, J. Heterocycl. Chem. 47, 1062 (2010)

    Article  CAS  Google Scholar 

  24. A. Rahmati, Chin. Chem. Lett. 21, 761 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We are grateful to the University of Sistan and Baluchestan Research Council for the partial support of this research.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, PO Box 98135-674, Zahedan, Iran

    Hamid Reza Shaterian, Marziyeh Sedghipour & Ebrahim Mollashahi

Authors
  1. Hamid Reza Shaterian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marziyeh Sedghipour
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ebrahim Mollashahi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hamid Reza Shaterian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shaterian, H.R., Sedghipour, M. & Mollashahi, E. Brønsted acidic ionic liquids catalyzed the preparation of 13-aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones and 3,4-dihydro-1H-benzo[b]xanthene-1,6,11(2H,12H)-triones. Res Chem Intermed 40, 1345–1355 (2014). https://doi.org/10.1007/s11164-013-1043-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1043-1

Keywords

Search

Navigation