Skip to main content
Log in

Urea-functionalized silica-coated Fe3−x Ti x O4 magnetic nanoparticles: as highly efficient and recyclable heterogeneous nanocatalyst for synthesis of 4H-chromene and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Novel urea-functionalized silica-coated magnetic core–shell Fe3−x Ti x O4 nanoparticles were prepared and fully characterized by different methods such as Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, field emission scanning electron microscopy, high-resolution transmission electron microscopy, vibrating sample magnetometer, X-ray diffraction, and thermogravimetric analyses. These magnetic nanoparticles have been explored as highly efficient and recoverable heterogeneous nanocatalyst for one-pot three-component reactions under mild conditions for the synthesis of diverse range of 5-oxo-dihydropyrano[3,2-c]chromenes known as coumarins and 1H-pyrazolo[1,2-b] phthalazine-5,10-diones in high yields. Simple isolation of the products, use of green solvent, and magnetically easy isolation and reusability of the catalyst with no significant loss of activity are the main advantages of the present method.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 3
Scheme 4
Fig. 8

Similar content being viewed by others

References

  1. L.M. Rossi, N.J.S. Costa, F.P. Silva, R.V. Goncalves, Nanotechnol. Rev. 2, 597 (2013)

    Article  CAS  Google Scholar 

  2. R.B.N. Baig, R.S. Varma, Chem. Commun. 49, 752 (2013). (and references cited therein)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  4. K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)

    Article  CAS  Google Scholar 

  5. P.T. Anastas, T. Williamson, Green Chemistry; Frontiers in Benign Chemical Synthesis and Process (Oxford University Press, Oxford, 1998)

    Google Scholar 

  6. P.T. Anastas, L.B. Bartlett, M.M. Kirchhof, T.C. Williamson, Catal. Today 55, 11 (2000)

    Article  CAS  Google Scholar 

  7. A. Maleki, S. Javanshir, M. Naimabadi, RSC Adv. 4, 30229 (2014)

    Article  CAS  Google Scholar 

  8. A. Maleki, M. Aghaei, N. Ghamari, Chem. Lett. 44, 259 (2015)

    Article  CAS  Google Scholar 

  9. A. Yamashita, F. Uejo, T. Yoda, T. Uchida, Y. Tanamura, T. Yamashita, N. Teramae, Nat. Mater. 3, 337 (2004)

    Article  Google Scholar 

  10. A. Maleki, A.H. Rezayan, Tetrahedron Lett. 55, 1848 (2014)

    Article  CAS  Google Scholar 

  11. A. Maleki, R. Paydar, RSC Adv. 5, 33177 (2015)

    Article  CAS  Google Scholar 

  12. A. Maleki, R. Rahimi, S. Maleki, Environ. Chem. Lett. 14, 195 (2016)

    Article  CAS  Google Scholar 

  13. M. Shakourian-Fard, A.H. Rezayan, S. Kheirjou, A. Bayat, M. Mahmoodi Hashemi, Bull. Chem. Soc. Jpn 87, 982 (2014)

    Article  CAS  Google Scholar 

  14. H. Itoh, S. Utamapanya, J.V. Stark, K.J. Klabunde, J.R. Schlup, Chem. Mater. 5, 71 (1993)

    Article  CAS  Google Scholar 

  15. A. Maleki, R. Rahimi, S. Maleki, Synth. Met. 194, 11 (2014)

    Article  CAS  Google Scholar 

  16. R.J. White, R. Luque, V.L. Budarin, J.H. Clark, D.J. Macquarrie, Chem. Soc. Rev. 38, 481 (2009)

    Article  CAS  Google Scholar 

  17. D.J. Cole-Hamilton, Science 299, 1702 (2003)

    Article  CAS  Google Scholar 

  18. F. Shi, M.K. Tse, M.M. Pohl, A. Bruckner, S. Zhang, M. Beller, Angew. Chem. Int. Ed. 46, 8866 (2007)

    Article  CAS  Google Scholar 

  19. D.H. Zhang, G.D. Li, J.X. Li, J.S. Chen, Chem. Commun. 29, 3414 (2008)

    Article  Google Scholar 

  20. A. Saxena, A. Kumar, S. Mozumdar, J. Mol. Catal. A Chem. 269, 35 (2007)

    Article  CAS  Google Scholar 

  21. A.T. Bell, Science 299, 1688 (2003)

    Article  CAS  Google Scholar 

  22. D. Guin, B. Baruwati, S.V. Manorama, Org. Lett. 9, 1419 (2007)

    Article  CAS  Google Scholar 

  23. S. Shyles, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)

    Article  Google Scholar 

  24. M.B. Gawande, A.K. Rathi, P.S. Branco, R.S. Varma, Appl. Sci. 3, 656 (2013). (and references cited therein)

    Article  CAS  Google Scholar 

  25. Y. Zhu, L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, Chem. Cat. Chem. 2, 365 (2010)

    CAS  Google Scholar 

  26. P. Wang, H. Liu, J. Niu, R. Li, J. Ma, Catal. Sci. Technol. 4, 1333 (2014)

    Article  CAS  Google Scholar 

  27. R. Tayebee, M.M. Amini, N. Abdollahi, A. Aliakbari, S. Rabiee, H. Ramshini, Appl. Catal. A Gen. 468, 75 (2013)

    Article  CAS  Google Scholar 

  28. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrera, J.M. Basset, Chem. Rev. 111, 3036 (2011). (and references cited therein)

    Article  CAS  Google Scholar 

  29. G. Schmid, Chem. Rev. 92, 1709 (1992)

    Article  CAS  Google Scholar 

  30. B. Karimi, M. Khalkhali, J. Mol. Catal. A Chem. 232, 113 (2005)

    Article  CAS  Google Scholar 

  31. I.K. Mbaraka, D.R. Radu, V.S. Lin, B.H. Shanks, J. Catal. 219, 329 (2003)

    Article  CAS  Google Scholar 

  32. S.R. Jetti, A. Bhatewara, T. Kadre, S. Jain, Chin. Chem. Lett. 25, 469 (2014)

    Article  CAS  Google Scholar 

  33. A. Maleki, E. Akhlaghi, R. Paydar, Appl. Organomet. Chem. 30, 382 (2016)

    Article  CAS  Google Scholar 

  34. M. Aghayee, M.A. Zolfigol, H. Keypour, M. Yarie, L. Mohammadi, Appl. Organomet. Chem. 30, 612 (2016)

    Article  CAS  Google Scholar 

  35. G.P. Ellis, The chemistry of heterocyclic compounds, in Chromenes, Chromenes and Chromenes, vol. 2, ed. by A. Weissberger, E.C. Taylor (Willey, New York, 1977), p. 13

    Google Scholar 

  36. E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, F.M.A.A. El-Taweel, Heterocycles 26, 903 (1987)

    Article  CAS  Google Scholar 

  37. A. Tanabe, H. Nakashima, O. Yoshida, N. Yamamoto, O. Tenmyo, T. Oki, J. Antibiot. 41, 1708 (1988)

    Article  CAS  Google Scholar 

  38. G. Shijay, H.T. Cheng, T. Chi, Y. Ching-Fa, Tetrahedron 64, 9143 (2008)

    Article  Google Scholar 

  39. A. Bolognese, G. Correale, M. Manfra, A. Lavecchia, O. Mazzoni, E. Novellino, P. La Colla, G. Sanna, R. Loddo, J. Med. Chem. 47, 849 (2004)

    Article  CAS  Google Scholar 

  40. T.A. Bayer, S. Schafer, H. Breyh, O. Breyhan, C. Wirths, G.A. Treiber, A vicious circle. Clin. Neuropathol. 25, 163 (2006)

    CAS  Google Scholar 

  41. N. Fokialakis, P. Magiatis, L. Chinou, S. Mitaka, F. Tillequin, Chem. Pharm. Bull. 50, 413 (2002)

    Article  CAS  Google Scholar 

  42. P. Beagley, M.A.L. Blackie, K. Chibale, C. Clarkson, R. Meijboom, J.R. Moss, P. Smith, H. Su, Dalton Trans. 15, 3046 (2003)

    Article  Google Scholar 

  43. F.M. Abdel Galil, B.Y. Riad, S.M. Sherif, M.H. Elnagdi, Chem. Lett. 11, 1123 (1982)

    Article  Google Scholar 

  44. D.C. Mungra, M.P. Patel, D.P. Rajani, R.G. Patel, Eur. J. Med. Chem. 46, 4192 (2011)

    Article  CAS  Google Scholar 

  45. S. Balalaie, S. Abdolmohammadi, Tetrahedron Lett. 48, 3299 (2007)

    Article  Google Scholar 

  46. M.M. Heravi, B. Alimadadi Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)

    Article  CAS  Google Scholar 

  47. M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)

    Article  CAS  Google Scholar 

  48. Y. Peng, G. Song, Catal. Commun. 8, 111 (2007)

    Article  CAS  Google Scholar 

  49. T.-S. Jin, L.-B. Liu, Y. Zhao, T.-S. Li, Synth. Commun. 35, 1859 (2005)

    Article  CAS  Google Scholar 

  50. G. Mohammadi Ziarani, A. Badiei, M. Azizi, P. Zarabadi, Iran. J. Chem. Chem. Eng. 30, 59 (2011)

    CAS  Google Scholar 

  51. B.N. Seshu, N. Pasha, R.K.T. Venkateswara, P.P.S. Sai, N. Lingaiah, Tetrahedron Lett. 49, 2730 (2008)

    Article  Google Scholar 

  52. S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)

    Article  CAS  Google Scholar 

  53. H. Nagabhushana, S.S. Saundalkar, L. Muralidhar, B.M. Nagab-hushana, C.R. Girija, D. Nagaraja, M.A. Pasha, V.P. Jayashankara, Chin. Chem. Lett. 22, 143 (2011)

    Article  CAS  Google Scholar 

  54. K. Niknam, A. Piran, Green Sustain. Chem. 3, 1 (2013)

    Article  Google Scholar 

  55. S. Grasso, G. DeSarro, N. Micale, M. Zappala, G. Puia, M. Baraldi, C. Demicheli, J. Med. Chem. 43, 2851 (2000)

    Article  CAS  Google Scholar 

  56. N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41, 3367 (1998)

    Article  CAS  Google Scholar 

  57. Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura, K. Kubo, Chem. Pharm. Bull. 38, 2179 (1990)

    Article  CAS  Google Scholar 

  58. H.W. Heine, M. Baclawski, S.M. Bonser, G.D. Wachob, J. Org. Chem. 41, 3221 (1976)

    Article  Google Scholar 

  59. L.P. Liu, J.M. Lu, M. Shi, Org. Lett. 9, 1303 (2007)

    Article  CAS  Google Scholar 

  60. D.S. Raghuvanshi, K.N. Singh, Tetrahedron Lett. 52, 5702 (2011)

    Article  CAS  Google Scholar 

  61. A. Azarifar, R. Nejat-Yami, M. AlKobaisi, D. Azarifar, J. Iran. Chem. Soc. 10, 439 (2012)

    Article  Google Scholar 

  62. A. Azarifar, R. Nejat-Yami, D. Azarifar, J. Iran. Chem. Soc. 10, 297 (2013)

    Article  CAS  Google Scholar 

  63. D. Azarifar, R. Nejat-Yami, F. Sameri, Z. Akrami, Lett. Org. Chem. 9, 435 (2012)

    Article  CAS  Google Scholar 

  64. D. Azarifar, Y. Abbasi, Synth. Commun. 46, 745 (2016)

    Article  CAS  Google Scholar 

  65. A. Maleki, Z. Alrezvani, S. Maleki, Catal. Commun. 69, 29 (2015)

    Article  CAS  Google Scholar 

  66. S. Yang, H. He, D. Wu, D. Chen, X. Liang, Z. Qin, M. Fan, J. Zhu, P. Yuan, Appl. Catal. B. Environ. 89, 527 (2009)

    Article  CAS  Google Scholar 

  67. X. Liang, Y. Zhong, S. Zhu, L. Ma, P. Yuan, J. Zhu, H. He, Z. Jiang, J. Hazard. Mater. 199–200, 247 (2012)

    Article  Google Scholar 

  68. M.B. Gawande, A.K. Rathi, I.D. Nogueira, R.S. Varma, P.S. Branco, Green Chem. 15, 1895 (2013)

    Article  CAS  Google Scholar 

  69. F. Nemati, M.M. Heravi, R. SaeediRadi, Chin. J. Catal. 33, 1825 (2012)

    Article  CAS  Google Scholar 

  70. K. Tabatabaeian, H. Heidari, M. Mamaghani, N.O. Mahmoodi, Appl. Organomet. Chem. 26, 56 (2012)

    Article  CAS  Google Scholar 

  71. F. Khorami, H.R. Shaterian, Chin. J. Catal. 35, 242 (2014)

    Article  CAS  Google Scholar 

  72. S.S. Mansoor, K. Logaiya, K. Aswin, P. Nithiya Sudhan, J. Taibah Univ. Sci. 9, 213 (2015)

    Article  Google Scholar 

  73. M. Khoobi, L. Ma’mani, F. Rezazadehb, Z. Zareieb, A. Foroumadia, A. Ramazanib, J. Mol. Catal. A Chem. 359, 74 (2012)

    Article  CAS  Google Scholar 

  74. R. Ghahremanzadeh, Gh Imani Shakibaei, A. Bazgir, Synlett 8, 1129 (2008)

    Google Scholar 

  75. M.R. Nabid, S.J. Tabatabaei Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 17, 159 (2010)

    Article  CAS  Google Scholar 

  76. A. Vafaee, A. Davoodnia, M. Pordel, M.R. Bozorgmehr, Orient. J. Chem. 31, 2153 (2015)

    Article  CAS  Google Scholar 

  77. A. Mulika, M. Deshmukha, D. Chandama, P. Patilb, S. Jagdalea, D. Patila, S. Sankpal, Der Pharma Chem 5, 19 (2013)

    Google Scholar 

  78. A. Montaghami, N. Montazeri, Orient. J. Chem. 30, 1361 (2014)

    Article  CAS  Google Scholar 

  79. H.J. Wang, J. Lu, Z.H. Zhang, Monatsh. Chem. 141, 1107 (2010)

    Article  CAS  Google Scholar 

  80. A. Alizadeh, M.M. Khodaei, M. Beygzadeh, D. Kordestani, M. Feyzi, Bull. Korean Chem. Soc. 33, 2546 (2012)

    Article  CAS  Google Scholar 

  81. G. Karthikeyana, A. Pandurangan, J. Mol. Catal. A Chem. 361–362, 58 (2012)

    Article  Google Scholar 

  82. M. Kidwai, R. Chauhan, J. Hetercyclic Chem. 51, 1689 (2014)

    Article  CAS  Google Scholar 

  83. B. Maleki, S. Barat Nam Chalaki, S. Sedigh Ashrafi, E.R. ezaeiSeresht, F. Moeinpour, A. Khojastehnezhad, R. Tayebee, Appl. Organomet. Chem. 29, 290 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors wish to thank the Research Council of Bu-Ali Sina University for financial support to carry out this research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Davood Azarifar.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Azarifar, D., Badalkhani, O., Abbasi, Y. et al. Urea-functionalized silica-coated Fe3−x Ti x O4 magnetic nanoparticles: as highly efficient and recyclable heterogeneous nanocatalyst for synthesis of 4H-chromene and 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives. J IRAN CHEM SOC 14, 403–418 (2017). https://doi.org/10.1007/s13738-016-0989-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-016-0989-5

Keywords

Navigation