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Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition

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Abstract

This paper reports an efficient heterogeneous catalyst based on sulfonic acid functionalization of magnetic nanoparticles. This new catalyst was prepared using the reaction between magnetic nanoparticles and sodium 2-bromoethane-1-sulfonate. Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA) was found as efficient catalyst for the synthesis of coumarin derivatives using Pechmann condensation under mild condition. This reaction was catalyzed by MNESA under solvent-free condition at 90 °C, to give the corresponding products in excellent yields. The catalyst is easily separated from the reaction condition and can be reused for several times with consistence in the activity.

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References

  1. J.A. Melero, J. Iglesiasa, G. Morales, Green Chem. 11, 1285 (2009)

    Article  CAS  Google Scholar 

  2. A.F. Lee, J.A. Bennett, J.C. Manayil, K. Wilson, Chem. Soc. Rev. 43, 7887 (2014)

    Article  CAS  Google Scholar 

  3. R. Ghanbaripour, I. Mohammadpoor-Baltork, M. Moghadam, A.R. Khosropour, S. Tangestaninejad, V. Mirkhani, Polyhedron 31, 721 (2012)

    Article  CAS  Google Scholar 

  4. R. Ghanbaripour, I. Mohammadpoor-Baltork, M. Moghadam, A.R. Khosropour, S. Tangestaninejad, V. Mirkhani, J. Iran. Chem. Soc. 9, 791 (2012)

    Article  CAS  Google Scholar 

  5. R. Mrówczyński, A. Nan, J. Liebscher, RSC Adv. 4, 5927 (2014)

    Article  Google Scholar 

  6. M.B. Gawande, P.S. Brancoa, R.S. Varma, Chem. Soc. Rev. 42, 3371 (2013)

    Article  CAS  Google Scholar 

  7. R. Ghanbaripour, M. Samadizadeh, G. Honarpisheh, M. Abdolmohammad, Synlett 26, 2117 (2015)

    Article  CAS  Google Scholar 

  8. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)

    Article  CAS  Google Scholar 

  9. H. Naeimi, S. Mohamadabadi, Dalton Trans. 43, 12967 (2014)

    Article  CAS  Google Scholar 

  10. C.S. Gill, B.A. Price, C.W. Jones, J. Catal. 251, 145 (2007)

    Article  CAS  Google Scholar 

  11. H. Mahmoudi, A.A. Jafari, ChemCatChem 5, 3743 (2013)

    Article  CAS  Google Scholar 

  12. A. Mobaraki, B. Movassagh, B. Karimi, ACS Comb. Sci. 16, 352 (2014)

    CAS  Google Scholar 

  13. B. Movassagh, L. Tahershamsi, A. Mobaraki, Tetrahedron Lett. 56, 1851 (2015)

    Article  CAS  Google Scholar 

  14. A. Khalafi-Nezhad, S. Mohammadi, ACS Comb. Sci. 15, 512 (2013)

    Article  CAS  Google Scholar 

  15. V.H. Pechmann, C. Duisberg, Chem. Ber. 17, 929 (1884)

    Article  Google Scholar 

  16. D.S. Bose, A.P. Rudradas, M.H. Babu, Tetrahedron Lett. 43, 9195 (2002)

    Article  Google Scholar 

  17. M.S. Manhas, S.N. Ganguly, S. Mukherjee, A.K. Jian, A.K. Bose, Tetrahedron Lett. 47, 2423 (2006)

    Article  CAS  Google Scholar 

  18. F. Rajabi, A. Feiz, R. Luque, Catal. Lett. 145, 1621 (2015)

    Article  CAS  Google Scholar 

  19. N.G. Khaligh, Catal. Sci. Technol. 2, 1633 (2012)

    Article  CAS  Google Scholar 

  20. H. Wang, Monatsh. Chem. 144, 411 (2013)

    Article  CAS  Google Scholar 

  21. Y. Zhang, A. Zhu, Q. Li, L. Li, Y. Zhao, J. Wang, RSC Adv. 4, 22946 (2014)

    Article  CAS  Google Scholar 

  22. M.S. Peng, J. Cai, Dyes Pigm. 79, 270 (2008)

    Article  CAS  Google Scholar 

  23. M. Roussaki, C.A. Kontogiorgis, D. Hadjipavlou-Litina, S. Hamilakis, A. Detsi, Bioorg. Med. Chem. Lett. 20, 3889 (2010)

    Article  CAS  Google Scholar 

  24. B. Tyagi, M.K. Mishra, R.V. Jasra, J. Mol. Catal. A: Chem. 286, 41 (2008)

    Article  CAS  Google Scholar 

  25. V.O. Iaroshenko, S. Ali, T.M. Babar, S. Dudkin, S. Mkrtchyan, N.H. Rama, A. Villinger, P. Langer, Tetrahedron Lett. 52, 373 (2011)

    Article  CAS  Google Scholar 

  26. J.R. Jonhnson, Org. React. 1, 210 (1942)

    Google Scholar 

  27. F. Jones, O. Piermatti, F. Pizzo, Heterocycles 43, 1257 (1996)

    Article  Google Scholar 

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

    Google Scholar 

  29. I. Yavari, R. Hekmat-Shoar, A. Zonouzi, Tetrahedron Lett. 39, 2391 (1998)

    Article  CAS  Google Scholar 

  30. R.O. Kennedy, R.D. Zhorenes, Coumarins: Biology, Applications and Mode of Action (Wiley, Chichester, 1997)

    Google Scholar 

  31. G.J. Fan, W. Mar, M.K. Park, E. Wook Choi, K. Kim, S. Kim, Bioorg. Med. Chem. Lett. 11, 2361 (2001)

    Article  CAS  Google Scholar 

  32. G. Cravotto, G.M. Nano, G. Palmisano, S. Tagliapietra, Tetrahedron Asymmetry 12, 707 (2001)

    Article  CAS  Google Scholar 

  33. N.A. Petasis, A.N. Butkevich, J. Organomet. Chem. 694, 1747 (2009)

    Article  CAS  Google Scholar 

  34. A. Alizadeh, R. Ghanbaripour, Synlett 25, 2777 (2014)

    Article  CAS  Google Scholar 

  35. D. Tejedor, L. Cotos, F. García-Tellado, J. Org. Chem. 78, 8853 (2013)

    Article  CAS  Google Scholar 

  36. N. Majumdar, K.A. Korthals, W.D. Wulff, J. Am. Chem. Soc. 134, 1357 (2012)

    Article  CAS  Google Scholar 

  37. A. Alizadeh, R. Ghanbaripour, L.G. Zhu, Synlett 25, 1596 (2014)

    Article  Google Scholar 

  38. T. Amanpour, K. Zangger, F. Belaj, A. Bazgir, D. Dallinger, C.O. Kappe, Tetrahedron 71, 7159 (2015)

    Article  CAS  Google Scholar 

  39. A. Alizadeh, R. Ghanbaripour, L.G. Zhu, Tetrahedron 70, 2048 (2014)

    Article  CAS  Google Scholar 

  40. H. Sharghi, M. Jokar, Heterocycles 71, 12 (2007)

    Google Scholar 

  41. E.C. Horning, Organic Synthesis, vol. III (Wiley, New York, 1955), p. 281

    Google Scholar 

  42. S.K. De, R.A. Gibbs, Synlett 16, 1231 (2005)

    Google Scholar 

  43. G.V.M. Sharma, J.J. Reddy, P.S. Lakshmi, P.R. Krishna, Tetrahedron Lett. 46, 6119 (2005)

    Article  CAS  Google Scholar 

  44. M.K. Potdur, S.S. Mohile, M.M. Salunkhe, Tetrahedron Lett. 42, 9285 (2001)

    Article  Google Scholar 

  45. Kandekar, A.C., Khadikar, B.M.: Synlett. 152 (2002)

  46. Y. Gu, J. Zhang, Z. Duan, Y. Deng, Adv. Synth. Catal. 347, 512 (2005)

    Article  CAS  Google Scholar 

  47. Hoz, A.D., Andres, M., Vazquez, E., Synlett. 602 (1999)

  48. E.A. Gunnewegh, A.J. Hoefnegal, H. Van Bekkum, J. Mol. Catal. A: Chem. 100, 87 (1995)

    Article  CAS  Google Scholar 

  49. S. Frere, V. Thiery, T. Besson, Tetrahedron Lett. 42, 2791 (2001)

    Article  CAS  Google Scholar 

  50. T. Li, Z. Zhang, F. Yang, C. Fu, J. Chem. Res. 1, 38 (1998)

    Article  Google Scholar 

  51. J.C. Rodriguez-Dominguez, G. Kirsch, Tetrahedron Lett. 47, 3279 (2006)

    Article  CAS  Google Scholar 

  52. F.K. Esfahani, D. Zareyee, R. Yousefi, ChemCatChem 6, 3333 (2014)

    Article  CAS  Google Scholar 

  53. B. Karimi, D. Zareyee, Org. Lett. 10, 3989 (2008)

    Article  CAS  Google Scholar 

  54. A. Khalafi-Nezhad, S. Mowlazadeh Haghighi, F. Panahi, ACS Sustain Chem. Eng. 1, 1015 (2013)

    Article  CAS  Google Scholar 

  55. D. Yuan, Q. Zhang, J. Dou, Catal. Commun. 11, 606 (2010)

    Article  CAS  Google Scholar 

  56. Y. Kang, L. Zhou, X. Li, J. Yuvan, J. Mater. Chem 21, 3704 (2011)

    Article  CAS  Google Scholar 

  57. S. Vahid Atghia, S. Sarvi Beigbaghlou, J. Nanostructure Chem. 3, 38 (2013)

    Article  Google Scholar 

  58. R. Kizil, J. Irudayaraj, K. Seetharaman, J. Agric. Food Chem. 50, 3912 (2002)

    Article  CAS  Google Scholar 

  59. F. M´arquez, T. Campo, M. Cotto, R. Polanco, R. Roque, P. Fierro, J.M. Sanz, E. Elizalde, C. Morant, Soft Nanosci. Lett. 1, 25 (2011)

    Article  Google Scholar 

  60. R.L. Siqueira, I.V.P. Yoshida, L.C. Pardini, M.A. Schiavon, Mater. Res. 10, 147 (2007)

    Article  CAS  Google Scholar 

  61. C. Wang, H. Daimon, S. Sun, Nano Lett. 9, 1493 (2009)

    Article  CAS  Google Scholar 

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Acknowledgments

We are thankful to Islamic Azad University central Tehran branch for partial support of this work.

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Correspondence to Marjaneh Samadizadeh.

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Samadizadeh, M., Nouri, S. & Kiani Moghadam, F. Magnetic nanoparticles functionalized ethane sulfonic acid (MNESA): as an efficient catalyst in the synthesis of coumarin derivatives using Pechmann condensation under mild condition. Res Chem Intermed 42, 6089–6103 (2016). https://doi.org/10.1007/s11164-016-2447-5

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