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Brønsted acidic ionic liquids catalyzed one-pot synthesis of benzoxanthene leuco-dye derivatives

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Abstract

Brønsted acidic ionic liquids, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate and N-methyl-2-pyrrolidonium hydrogen sulfate, are found to be efficient catalysts for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-dione, 3,4-dihydro-2H-benzo[b]xanthene-1,6,11(12H)-trione, and aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraone derivatives under solvent-free conditions. The mentioned ionic liquids are recyclable catalysts and were reused several times without any significant loss of their activities. High conversions, shorter reaction times, cleaner reaction, and simple experimental and work-up procedures are advantages.

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References

  1. D. Marzin, D. Kirkland, Mutat. Res. 560, 41 (2004)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. C. Wright, G.V. Ullas, J. Labelled, Compd. Radiopharm. 45, 1265 (2002)

    Article  CAS  Google Scholar 

  4. R.M. Fusaro, W.J. Runge, J.A. Johnson, Int. J. Dermatol. 11, 67 (1972)

    Article  CAS  Google Scholar 

  5. M.M.D. Oliveira, M.C.F. Linardi, M.R.P. Sampaio, J. Pharm. Sci. 67, 562 (1978)

    Article  Google Scholar 

  6. B. Søballe, K.P. Robert, Microbiology 145, 1817 (1999)

    Article  Google Scholar 

  7. 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 

  8. A.M. Inamuddin, Green solvents I: properties and applications in chemistry (Springer, London, 2012)

    Google Scholar 

  9. H.R. Shaterian, A.R. Oveisi, J. Iran. Chem. Soc. 8, 545 (2011)

    Article  CAS  Google Scholar 

  10. M.J. Earle, J.M.S.S. Esperança, M.A. Gilea, J.N. Canongia Lopes, L.P.N. Rebelo, J.W. Magee, K.R. Seddon, J.A. Widegren, Nature 439, 831 (2006)

    Article  CAS  Google Scholar 

  11. A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes, J.H. Davis, J. Am. Chem. Soc. 124, 5962 (2002)

    Article  CAS  Google Scholar 

  12. R.D. Rogers, K. Seddon, Ionic liquids: industrial applications for green chemistry (Oxford University Press, Oxford, 2002)

  13. L.Q. Wu, Y.F. Wu, C.G. Yang, L.M. Yang, L.J. Yang, J. Braz. Chem. Soc. 221, 941 (2010)

    Article  Google Scholar 

  14. L. Wu, J. Zhang, L. Fang, C. Yang, F. Yan, Dyes Pigment. 86, 93 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  18. Z. Noroozi Tisseh, C. Azimi, P. Mirzaei, A. Bazgir, Dyes Pigment. 79, 273 (2008)

    Article  Google Scholar 

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Acknowledgments

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

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Authors and Affiliations

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

    Hamid Reza Shaterian & Kobra Azizi

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  1. Hamid Reza Shaterian
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  2. Kobra Azizi
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Correspondence to Hamid Reza Shaterian.

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Shaterian, H.R., Azizi, K. Brønsted acidic ionic liquids catalyzed one-pot synthesis of benzoxanthene leuco-dye derivatives. Res Chem Intermed 41, 409–417 (2015). https://doi.org/10.1007/s11164-013-1202-4

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  • DOI: https://doi.org/10.1007/s11164-013-1202-4

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