Advertisement

Research on Chemical Intermediates

, Volume 45, Issue 10, pp 5067–5089 | Cite as

Magnetic nanoparticles tris(hydrogensulfato) boron as an efficient heterogeneous acid catalyst for the synthesis of α,ά-benzylidene bis(4-hydroxycoumarin) derivatives under solvent-free condition

  • Payam Hayati
  • Khadijeh Eghbali
  • Ramin RezaeiEmail author
Article
  • 231 Downloads

Abstract

Nano-ferrite supported tris(hydrogensulfato) boron [Fe3O4@B(HSO4)3] was prepared by entrapping Fe3O4 magnetic nanoparticles as the core and tris(hydrogensulfato) boron B(HSO4)3 as the outer shell. This effective and magnetically recoverable catalyst was employed for the synthesis of α,ά-benzylidene bis(4-hydroxycoumarin) derivatives through the reaction of an aromatic aldehyde and 4-hydroxycoumarin under solvent-free conditions. This acid catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction analysis, scanning electron microscopy, transmission electron microscopy, thermal gravimetric analysis and differential scanning calorimetry, energy-dispersive X-ray spectroscopy, Brunauer–Emmett–Teller analysis, Barret–Joyner–Halenda analysis, vibrating sample magnetometer and titration.

Keywords

Magnetic nanoparticles Multicomponent reactions Heterogeneous catalysts Biscoumarins Tris (hydrogensulfato) boron 

Notes

Acknowledgements

The authors acknowledge Firoozabad University Research Council for partial financial support.

References

  1. 1.
    J.A. Melero, R.V. Grieken, G. Morales, Chem. Rev. 106, 3790 (2006)CrossRefPubMedGoogle Scholar
  2. 2.
    J.A. Melero, J. Iglesias, G. Morales, Green Chem. 11, 1285 (2009)CrossRefGoogle Scholar
  3. 3.
    J. Lu, P.H. Toy, Chem. Rev. 109, 815 (2009)CrossRefPubMedGoogle Scholar
  4. 4.
    S.J. Yuan, X.H. Dai, Appl. Catal. B Environ. 154, 252 (2014)CrossRefGoogle Scholar
  5. 5.
    K. Pandey, R.V. Jayaram, M.B. Gawande, R.K. Pandey, R.V. Jayaram, Catal. Sci. Technol. 2, 1113 (2012)Google Scholar
  6. 6.
    M.B. Gawande, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 3371 (2013)CrossRefPubMedGoogle Scholar
  7. 7.
    M. Fernández-García, J.A. Rodriguez, Metal Oxide Nanoparticles, Encyclopedia of Inorganic and Bioinorganic, Chemistry (Wiley, Hoboken, 2011)Google Scholar
  8. 8.
    R.M. Cornell, U. Schwartmann, The Iron Oxide: Structure, Properties, Reactions, Currences and Uses (Wiley, Weinheim, 2003)CrossRefGoogle Scholar
  9. 9.
    W. Wu, Z. Wu, T. Yu, C. Jiang, W.-S. Kim, Sci. Technol. Adv. Mater 16, 023501 (2015)CrossRefPubMedPubMedCentralGoogle Scholar
  10. 10.
    M.B. Gawande, A. Goswami, T. Asefa, H. Guo, A.V. Biradar, D.-L. Peng, R. Zboril, R.S. Varma, Chem. Soc. Rev. 44, 7431 (2015)CrossRefGoogle Scholar
  11. 11.
    A. Hu, G.T. Yee, W. Lin, J. Am. Chem. Soc. 127, 12486 (2005)CrossRefPubMedGoogle Scholar
  12. 12.
    A. Schätz, M. Hager, O. Reiser, Adv. Funct. Mater. 19, 2109 (2009)CrossRefGoogle Scholar
  13. 13.
    M.A. Ghasemzadeh, J. Safaei-Ghomi, S. Zahedi, J. Serb. Chem. Soc. 78, 769 (2013)CrossRefGoogle Scholar
  14. 14.
    K. Karami, S. Dehghani Najvani, N. Haghighat Naeini, P. Hervés, Chin. J. Catal. 36, 1047 (2015)CrossRefGoogle Scholar
  15. 15.
    M.A. Ghasemzadeh, Acta Chim. Slov. 62, 977 (2015)CrossRefPubMedGoogle Scholar
  16. 16.
    M.A. Ghasemzadeh, Quim. Nova 1, 47 (2017)Google Scholar
  17. 17.
    R.B. Kistler, C. Helvaci, Boron and borates, in Industrial minerals and rocks, 6th edn., ed. by D.D. Carr (SME, Littleton, 1994), p. 171Google Scholar
  18. 18.
    I. Tsuyumoto, T. Oshio, J. Wood Chem. Technol. 29, 277 (2009)CrossRefGoogle Scholar
  19. 19.
    Method 3052 microwave assisted acid digestion of siliceous and organically based matrices (PDF) US EPA 2015-06-22Google Scholar
  20. 20.
    J. Dempsey (2009) [1998] “BORAX” dempsey’s forge retrieved 2010-07-23 (2009)Google Scholar
  21. 21.
    F. Prager, Science becomes a toy-silly putty. loti.com. Rewind the fifites. Retrieved 06 July 2013Google Scholar
  22. 22.
    A.R. Kiasat, M. Fallah-Mehrjardi, J. Braz. Chem. Soc. 19, 1595 (2008)CrossRefGoogle Scholar
  23. 23.
    Z. Karimi-Jaberi, B. Pooladian, Monatshefte für Chemie. 144, 659 (2013)CrossRefGoogle Scholar
  24. 24.
    Z. Karimi-Jaberi, A. Jaafarizadeh, Res. Chem. Intermed. 41, 4913 (2015)CrossRefGoogle Scholar
  25. 25.
    Z. Karimi-Jaberi, M.R. Nazarifar, B. Pooladian, Chin. Chem. Lett. 23, 781 (2012)CrossRefGoogle Scholar
  26. 26.
    M. Soheilizad, M. Adib, S. Sajjadifar, Monatshefte für Chemie 144, 1353 (2014)CrossRefGoogle Scholar
  27. 27.
    H.R. Safaei, M. Davoodi, M. Shekouhy, Synth. Commun. 43, 2178 (2013)CrossRefGoogle Scholar
  28. 28.
    S.J. Saghanezhad, H.R. Safaei, J. Serb. Chem. Soc. 78, 1481 (2013)CrossRefGoogle Scholar
  29. 29.
    A. Khalafi-Nezhad, H. Foroughi, M.M. Doroodmand, F. Panahi, J. Mater. Chem. 21, 12842 (2011)CrossRefGoogle Scholar
  30. 30.
    M. Farahi, B. Karami, R. Keshavarz, F. Khosravian, RSC Adv. 7, 46644 (2017)CrossRefGoogle Scholar
  31. 31.
    A. Maresca, A. Scozzafava, C.T. Supuran, Bioorg. Med. Chem. Lett. 20, 7255 (2010)CrossRefPubMedGoogle Scholar
  32. 32.
    N. Vukovic, S. Sukdolak, S. Solujic, N. Niciforovic, Food Chem. 120, 1011 (2010)CrossRefGoogle Scholar
  33. 33.
    F. Carta, A. Maresca, A. Scozzafava, C.T. Supuran, Bioorg. Med. Chem. 20, 2266 (2012)CrossRefPubMedGoogle Scholar
  34. 34.
    R. Okenne, R.D. Thomes, Coumarins: Biology, Application, and Modes of Action (Wiley, Chichester, 1997)Google Scholar
  35. 35.
    M. Zahradnik, The Production and Application of Fluorescent Brightening Agents (Wiley, Chichester, 1992)Google Scholar
  36. 36.
    C. Ranjitha, K.K. Vijayan, V.K. Praveen, N.S. Saleesh Kumar, Spectrochim Acta A 75, 1610 (2010)CrossRefGoogle Scholar
  37. 37.
    M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268, 76 (2007)CrossRefGoogle Scholar
  38. 38.
    J.M. Khurana, S. Kumar, Monatsh. Chem. 141, 561 (2010)CrossRefGoogle Scholar
  39. 39.
    J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)CrossRefGoogle Scholar
  40. 40.
    H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)CrossRefGoogle Scholar
  41. 41.
    B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 4343 (2012)CrossRefGoogle Scholar
  42. 42.
    W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141, 1651 (2011)CrossRefGoogle Scholar
  43. 43.
    K. Parvanak Boroujeni, P. Ghasemi, Z. Rafienia, Monatsh Chem. 145, 1651 (2014)CrossRefGoogle Scholar
  44. 44.
    M.M. Heravi, F. Nahavandi, S. Sadjadi, H.A. Oskooie, F.F. Bamoharram, Synth. Commun. 145, 498 (2010)CrossRefGoogle Scholar
  45. 45.
    K. Parvanak Boroujeni, S. Hadizadeh, S. Hasani, A. Fadavi, M. Shahrokh, Acta Chim. Slov. 64, 692 (2017)CrossRefPubMedGoogle Scholar
  46. 46.
    J. Albadi, A. Mansournezhad, S. Salehnasab, Res. Chem. Intermed. 41, 5713 (2015)CrossRefGoogle Scholar
  47. 47.
    S. Rahmani, B. Zeynizadeh, Res. Chem. Intermed. 45, 1227 (2019)CrossRefGoogle Scholar
  48. 48.
    R. Rezaei, F. Moezzi, M.M. Doroodmand, Chin. Chem. Lett. 25, 183 (2014)CrossRefGoogle Scholar
  49. 49.
    R. Rezaei, M.R. Sheikhi, Res. Chem. Intermed. 41, 1283 (2015)CrossRefGoogle Scholar
  50. 50.
    F. Gholamian, M. Shabanian, M. Shahrokh, J. Clust. Sci. 24, 177 (2013)CrossRefGoogle Scholar
  51. 51.
    L. Boroica, D. Radu, R. Medianu, J. Optoelectron. & Adv. Mater. 10, 3217 (2008)Google Scholar
  52. 52.
    A. Alinasab Amiri, S. Javanshir, Z. Dolatkhah, M.G. Dekamin, New J. Chem. 39, 9665 (2015)CrossRefGoogle Scholar
  53. 53.
    M.A. Ghasemzadeh, J. Safaei-Ghomi, H. Molaei, C. R. Chimie. 15, 969 (2012)CrossRefGoogle Scholar
  54. 54.
    S.H. Dewi, W.A. Adi, J. Phys. Conf. Ser. 1091, 012021 (2018)CrossRefGoogle Scholar
  55. 55.
    A. Ruíz-Baltazar, R. Esparza, G. Rosas, R. Pérez, J Nanomater. 16, 1 (2015)Google Scholar
  56. 56.
    E. Moroydor Derun, P. Gurses, M. Yildirim, A.S. Kipcak, T. Ibroska, S. Piskin, Int. Sch. Sci. Res. Innov. 8, 565 (2014)Google Scholar
  57. 57.
    M.B. Gawande, A.K. Rathi, I.D. Nogueira, R.S. Varma, P.S. Branco, Green Chem. 15, 1895 (2013)CrossRefGoogle Scholar
  58. 58.
    F. Sevim, F. Demir, M. Bilen, H. Okur, Korean J. Chem. Eng. 23, 736 (2006)CrossRefGoogle Scholar
  59. 59.
    K. Onar. M.E Yakinci, Journal of Physics: 9th International Conference on Magnetic and Superconducting Materials (MSM15) 667, Antalya, Turkey, 30 April to 3 May 2015Google Scholar
  60. 60.
    S. Brunauer, L.S. Deming, W.E. Deming, E. Teller, J. Am. Chem. Soc. 62, 1723 (1940)CrossRefGoogle Scholar
  61. 61.
    G. Leofanti, M. Padovan, G. Tozzola, B. Venturelli, Catal. Today 41, 207 (1998)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Persian Gulf Science and Technology ParkNano Gostaran Navabegh Fardaye Dashtestan CompanyBorazjanIran
  2. 2.Department of Chemistry, Firoozabad BranchIslamic Azad UniversityFiroozabadIran

Personalised recommendations