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The synthesis of coumarin derivatives using choline chloride/zinc chloride as a deep eutectic solvent

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Abstract

In this work, choline chloride/zinc chloride was employed as a deep eutectic solvent (DES) in the green synthesis of coumarin derivatives using Knoevenagel condensation. Coumarins are important organic structures with useful application in various fields. The procedure consisted of the reaction between salicylaldehyde derivatives and active methylene compounds (dimethyl malonate, ethyl cyano acetate and ethyl 3-oxo-3-phenylpropanoate) to produce various coumarin derivatives. The general procedure is easy because of simple preparation and isolation of desired products. Moreover, the method is environmental friendly because of avoiding use of toxic solvents or hazardous catalysts. In the presented method, only 10 % of choline chloride/zinc chloride was employed as a non-toxic and biologically degradable media. All reactions have been completed under mild conditions with high yields (61–96 %). The employed DES plays both roles of solvent and catalyst in this reaction. Moreover, it has been reused four times in this procedure without important decreasing in the yield of reaction.

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References

  1. R. Okennedy, R.D. Thornes, Coumarins: biology, applications and mode of action, 1st edn. (Wiley, Chichester, 1997), pp. 103–136

    Google Scholar 

  2. M. Maheswara, V. Siddaiah, G.L.V. Damu, Y.K. Rao, C.V. Rao, J. Mol. Catal. 255, 49 (2006)

    Article  CAS  Google Scholar 

  3. S.M. Sethna, R. Phadke, Org. React. 7, 1 (1953)

    Google Scholar 

  4. G. Jones, Org. React. 15, 204 (1967)

    CAS  Google Scholar 

  5. F. Bigi, L. Chesini, R. Maggi, G. Sartori, J. Org. Chem. 64, 10334 (1999)

    Google Scholar 

  6. B.J. Donnelly, D.M.X. Donnelly, A.M.O. Sullivan, Tetrahedron 24, 2617 (1968)

    Article  CAS  Google Scholar 

  7. J.R. Johnson, Org. React. 1, 210 (1942)

    Google Scholar 

  8. R.L. Shirner, Org. React. 1, 1 (1942)

    Google Scholar 

  9. I. Yavari, R. Hekmat-shoar, A. Zonuzi, Tetrahedron Lett. 39, 2391 (1998)

    Article  CAS  Google Scholar 

  10. B.M. Trost, Comprehensive organic synthesis (Pergamon, Oxford, 1991), pp. 341–394

    Google Scholar 

  11. B.C. Ranu, R. Jana, Eur. J. Org. Chem. 3767 (2006)

  12. C. Li, Chem. Rev. 93, 2023 (1993)

    Article  CAS  Google Scholar 

  13. A. Hoz, A. Moreno, E. Vazquez, Synlett 608 (1999)

  14. N. Britto, V.G. Gore, R.S. Mali, A.C. Ranade, Synth. Commun. 19, 1899 (1989)

    Article  CAS  Google Scholar 

  15. B.P. Bandgar, L.S. Uppalla, D.S. Kurule, Green Chem. 1,  243 (1999)

    Article  CAS  Google Scholar 

  16. P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39, 3772 (2000)

    Article  CAS  Google Scholar 

  17. S.B. Phadtare, K.J. Jarag, G.S. Shankarling, Dyes. Pigm. 97, 105 (2013)

    Article  CAS  Google Scholar 

  18. I. Bandres, R. Alcalde, C. Lafuente, M. Atilhan, S. Aparicio, J. Phys. Chem. B 115, 12499 (2011)

    Article  CAS  Google Scholar 

  19. S.L. Perkins, P. Painter, C.M. Colina, J. Phys. Chem. B. 117, 10250 (2013)

    Article  CAS  Google Scholar 

  20. D. Saberi, J. Akbari, S. Mahdudi, A. Heydari, J. Mol. Liq. 196, 208 (2014)

    Article  CAS  Google Scholar 

  21. Q. Zhang, K.D. Vigier, S. Royer, F. Jerome, Chem. Soc. Rev. 41, 7108 (2012)

    Article  CAS  Google Scholar 

  22. B.S. Singh, H.R. Lobo, D.V. Pinjari, K.J. Jarag, A.B. Pandit, G.S. Shankarling, Ultrason. Sonochem. 20, 287 (2013)

    Article  CAS  Google Scholar 

  23. I. Hawkins, S.T. Handy, Tetrahedron 69, 9200 (2013)

    Article  CAS  Google Scholar 

  24. A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, R.K. Rasheed, J. Am. Chem. Soc. 126, 9142 (2004)

    Article  CAS  Google Scholar 

  25. N. Azizi, E. Gholibeglo, M. Babapour, H. ghafuri, S.M. Bolourtchian, Compet. Rendus Chimie 15, 768 (2012)

    Article  CAS  Google Scholar 

  26. N. Jain, A. Kumar, S. Chauhan, Tetrahedron 61, 1015 (2005)

    Article  CAS  Google Scholar 

  27. Y. Cai, Y. Peng, G. Song, Catal. Lett. 109, 61 (2006)

    Article  CAS  Google Scholar 

  28. T. Welton, Chem. Rev. 99, 2071 (1999)

    Article  CAS  Google Scholar 

  29. N. Azizi, S. Dezfooli, M.M. Hashemi, Compet. Rendus Chimie 16, 1098 (2013)

    Article  CAS  Google Scholar 

  30. H. Tavakol, S. Hatami, S. Ghammamy, G. Rezaei-Behbahani, F. Shabani, Heteroat. Chem. 20, 398 (2009)

    Article  CAS  Google Scholar 

  31. F. Keshavarzipour, H. Tavakol, Catal. Lett. 145, 1062 (2015)

    Article  CAS  Google Scholar 

  32. Z. Mirjafary, H. Saeidian, F.M. Moghaddam, Trans. C Chem. Chem. Eng. 16, 12 (2009)

    Google Scholar 

  33. H. Valizadeh, M. Mahmoodian, H. Gholipour, J. Heterocycl. Chem. 48, 799 (2011)

    Article  CAS  Google Scholar 

  34. A. Shockravi, H. Shargi, H. Valizadeh, M.M. Heravi, Sulfur Silicon Relat. Elem. 177, 2555 (2002)

    Article  CAS  Google Scholar 

  35. J.R. Harjani, S.J. Nara, M.M. Salunkhe, Tetrahedron Lett. 43, 1127 (2002)

    Article  CAS  Google Scholar 

  36. H. Valizadeh, S. Vaghefi, Syn. Comm. 39, 1666 (2009)

    Article  CAS  Google Scholar 

  37. N.B. Darvatkar, A.R. Deorukhkar, S.V. Bhilare, D.G. Raut, M.M. Salunkhe, Syn. Commun. 38, 3508 (2008)

    Article  CAS  Google Scholar 

  38. A.P. Abbott, G. Capper, D.L. Davies, H. Munro, R.K. Rasheed, V. Tambyrajah, Chem. Commun. 201 (2001)

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Acknowledgments

This work was supported by the research affairs of Isfahan University of technology.

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Authors and Affiliations

  1. Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Iran

    Fariba Keshavarzipour & Hossein Tavakol

Authors
  1. Fariba Keshavarzipour
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  2. Hossein Tavakol
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Correspondence to Hossein Tavakol.

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Keshavarzipour, F., Tavakol, H. The synthesis of coumarin derivatives using choline chloride/zinc chloride as a deep eutectic solvent. J IRAN CHEM SOC 13, 149–153 (2016). https://doi.org/10.1007/s13738-015-0722-9

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  • DOI: https://doi.org/10.1007/s13738-015-0722-9

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