Citation: Hossein Eshghi, Ali Javid, Amir Khojastehnezhad, Farid Moeinpour, Fatemeh F. Bamoharram d, Mehdi Bakavoli, Masoud Mirzaei. Preyssler heteropolyacid supported on silica coated NiFe₂O₄ nanoparticles for the catalytic synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones[J]. Chinese Journal of Catalysis, ;2015, 36(3): 299-307. doi: 10.1016/S1872-2067(14)60265-5 shu

Preyssler heteropolyacid supported on silica coated NiFe₂O₄ nanoparticles for the catalytic synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones

1.
a Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad, Iran;

Corresponding author: Ali Javid, Amir Khojastehnezhad,
Received Date: 19 October 2014
Available Online: 12 December 2014

A novel magnetic acidic catalyst comprising Preyssler (H₁₄[NaP₅W₃₀O₁₁₀]) heteropoly acid supported on silica coated nickel ferrite nanoparticles (NiFe₂O₄@SiO₂) was prepared. The catalyst was characterized by Fourier transform infrared, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy dispersive spectrum, VSM and particle size neasurement. Its catalytic activity was investigated for the synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones derivatives by the Biginelli reaction. With the catalyst, the reactions occurred in less than 1 h with good to excel-lent yields. More importantly, the catalyst was easily separated from the reaction mixture by an external magnet and reused at least five times without degradation in the activity.
- Preyssler,
- Nickel ferrite nanoparticles,
- Magnetically green catalyst,
- Bis(dihydropyrimidinone)benzene,
- 3,4-Dihydropyrimidin-2(1H)-ones
1. [1]
  [1] Saiyed Z M, Telang S D, Ramchand C N. BioMagn Res Technol, 2003, 1: 2
2. [2]
  [2] Sahoo S K, Labhasetwar V. Drug Discovery Today, 2003, 8: 1112
3. [3]
  [3] Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J M. Chem Rev, 2011, 111: 3036
4. [4]
  [4] Li P H, Wang L, Zhang L, Wang G W. Adv Synth Catal, 2012, 354: 1307
5. [5]
  [5] Wittmann S, Schätz A, Grass R N, Stark W J, Reiser O. Angew Chem Int Ed, 2010, 49: 1867
6. [6]
  [6] Kaboudin B, Mostafalu R, Yokomatsu T. Green Chem, 2013, 15: 2266
7. [7]
  [7] Wang Y H, Lee J K. J Mol Catal A, 2007, 263: 163
8. [8]
  [8] Rossi L M, Silva F P, Vono L L R, Kiyohara P K, Duarte E L, Itri R, Landers R, Machado G. Green Chem, 2007, 9: 379
9. [9]
  [9] Yi D K, Lee S S, Ying J Y. Chem Mater, 2006, 18: 2459
10. [10]
  [10] Polshettiwar V, Varma R S. Org Biomol Chem, 2009, 7: 37
11. [11]
  [11] Aschwanden L, Panella B, Rossbach P, Keller B, Baiker A. ChemCatChem, 2009, 1: 111
12. [12]
  [12] Oliveira R L, Kiyohara P K, Rossi L M. Green Chem, 2010, 12: 144
13. [13]
  [13] Karimi B, Farhangi E. Chem Eur J, 2011, 17: 6056
14. [14]
  [14] Schätz A, Grass R N, Stark W J, Reiser O. Chem Eur J, 2008, 14: 8262
15. [15]
  [15] Tucker-Schwartz A K, Garrell R L. Chem Eur J, 2010, 16: 12718
16. [16]
  [16] Karimi B, Farhangi E. Adv Synth Catal, 2013, 355: 508
17. [17]
  [17] Rostamnia S, Lamei K, Mohammadquli M, Sheykhan M, Heydari A. Tetrahedron Lett, 2012, 53: 5257
18. [18]
  [18] Sheykhan M, Mohammadnejad H, Akbari J, Heydari A. Tetrahedron Lett, 2012, 53: 2959
19. [19]
  [19] Mamani L, Heydari A, Sheykhan M. Appl Catal A, 2010, 384: 122
20. [20]
  [20] Wang S G, Zhang Z H, Liu B, Li J L. Catal Sci Technol, 2013, 3: 2104
21. [21]
  [21] Rafiee E, Eavani S. Green Chem, 2011, 13: 2116
22. [22]
  [22] Rafiee E, Eavani S. J Mol Catal A, 2013, 373: 30
23. [23]
  [23] Rafiee E, Eavani S, Khodayari M. Chin J Catal (催化学报), 2013, 34: 1513
24. [24]
  [24] Chaudhuri A, Mandal M, Mandal K. J Alloys Compd, 2009, 487: 698
25. [25]
  [25] Köseoğlu Y, Baykal A, Toprak M S, Gözüak F, Başaran A C, Aktaş B. J Alloys Compd, 2008, 462: 209
26. [26]
  [26] Hou X Y, Feng J, Xu X D, Zhang M L. J Alloys Compd, 2010, 491: 258
27. [27]
  [27] Goldman A. Modern Ferrite Technology. New York: Van Nostrand Reinhold, 1990
28. [28]
  [28] Hekmatshoar R, Sadjadi S, Shiri S, Heravi M M, Beheshtiha Y S. Synth Commun, 2009, 39: 2549
29. [29]
  [29] Hafizi A, Ahmadpour A, Heravi M M, Bamoharram F F. Pet Sci Technol, 2014, 32: 1022
30. [30]
  [30] Wu S S, Liu P, Leng Y, Wang J. Catal Lett, 2009, 132: 500
31. [31]
  [31] Javid A, Khojastehnezhad A, Heravi M M, Bamoharram F F. Syn React Inorg Met Org, 2012, 42: 14
32. [32]
  [32] Hafizi A, Ahmadpour A, Heravi M M, Bamoharram F F, Khosroshahi M. Chin J Catal (催化学报), 2012, 33: 494
33. [33]
  [33] Bamoharram F F, Heravi M M, Ebrahimi J, Ahmadpour A, Zebarjad M. Chin J Catal (催化学报), 2011, 32: 782
34. [34]
  [34] Madhusudhan Rao P, Wolfson A, Kababya S, Vega S, Landau M V. J Catal, 2005, 232: 210
35. [35]
  [35] Ghiaci M, Zarghani M, Khojastehnezhad A, Moeinpour F. RSC Adv, 2014, 4: 15496
36. [36]
  [36] Ghiaci M, Zarghani M, Moeinpour F, Khojastehnezhad A. Appl Organomet Chem, 2014, 28: 589
37. [37]
  [37] Davoodnia A, Khojastehnezhad A, Tavakoli-Hoseini N. Bull Korean Chem Soc, 2011, 32: 2243
38. [38]
  [38] Khojastehnezhad A, Moeinpour F, Davoodnia A. Chin Chem Lett, 2011, 22: 807
39. [39]
  [39] Khojastehnezhad A, Rahimizadeh M, Eshghi H, Moeinpour F, Bakavoli M. Chin J Catal (催化学报), 2014, 35: 376
40. [40]
  [40] Eshghi H, Khojastehnezhad A, Moeinpour F, Bakavoli M, Seyadi S M, Abbasi M. RSC Adv, 2014, 4: 39782
41. [41]
  [41] Khojastehnezhad A, Rahimizadeh M, Moeinpour F, Eshghi H, Bakavoli M. Compt R C, 2014, 17: 459
42. [42]
  [42] Gharib A, Jahangir M, Scheeren J W. Polish J Chem Technol, 2011, 13(2): 11
43. [43]
  [43] Hamadi H, Kootia M, Afshari M, Ghiasifar Z, Adibpour N. J Mol Catal A, 2013, 373: 25
44. [44]
  [44] Vivekanandhan S, Venkateswarlu M, Carnahan D, Misra M, Mohanty A K, Satyanarayana N. Ceramics Int, 2013, 39: 4105
45. [45]
  [45] Wang H X, Zhang W, Zhang F L, Cao Y, Su W H. J Magn Magn Mater, 2008, 320: 1916
46. [46]
  [46] Tu S J, Zhu X T, Fang F, Zhang X J, Zhu S L, Li T J, Shi D Q, Wang X S, Ji S J. Chin J Chem, 2005, 23: 596
47. [47]
  [47] Azizian J, Mohammadi M K, Firuzi O, Mirza B, Miri R. Chem Biol Drug Des, 2010, 75: 375
48. [48]
  [48] Zeinali-Dastmalbaf M, Davoodnia A, Heravi M M, Tavakoli-Hoseini N, Khojastehnezhad A, Zamani H A. Bull Korean Chem Soc, 2011, 32: 656
49. [49]
  [49] Niknam Kh, Daneshvar N. Heterocycles, 2007, 71: 373
50. [50]
  [50] Niknam Kh, Ali Zolfigol M, Hossieninejad Z, Daneshvar N. Chin J Catal (催化学报), 2007, 28: 591
51. [51]
  [51] Hasaninejad A, Zare A, Jafari F, Moosavi-Zare A R. E-J Chem, 2009, 6: 459
52. [52]
  [52] Tajbakhsh M, Ranjbar Y, Masuodi A, Khaksar S. Chin J Catal (催化学报), 2012, 33: 1542
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Preyssler heteropolyacid supported on silica coated NiFe2O4 nanoparticles for the catalytic synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones

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通讯作者: 陈斌, bchen63@163.com

Preyssler heteropolyacid supported on silica coated NiFe₂O₄ nanoparticles for the catalytic synthesis of bis(dihydropyrimidinone)benzene and 3,4-dihydropyrimidin-2(1H)-ones