Imidazole functionalized magnetic Fe3O4 nanoparticles as a novel heterogeneous and efficient catalyst for synthesis of dihydropyrimidinones by Biginelli reaction

Abstract

Dihydropyrimidinone derivatives were synthesized in moderate to high yields in one-pot three-component condensation reactions from the corresponding aldehydes, 1,3-dicarbonyl compounds, and urea in the presence of catalytic amounts of imidazole functionalized on magnetic nanoparticles as an efficient, non-toxic, reusable, and easily available catalyst under solvent-free conditions at 80 °C. Compared to the classical Biginelli reaction, this new method consistently has the advantage of excellent yields, short reaction times, and methodological simplicity. Furthermore, the nanomagnetic catalyst could be readily handled and removed from the reaction mixture via application of an external magnet, allowing straightforward recovery and reuse.

Graphical Abstract

.

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

Fig. 1
Fig. 2
Fig. 3

References

  1. 1.

    Biginelli P (1893) Gazz Chim Ital 23:360

    Google Scholar 

  2. 2.

    Rovnyak GC, Kimball SD, Beyer B, Cucinotta G, Dimarco JD, Gougoutas J, Hedberg AO, Malley M, McCarthy JP, Zhang R, Moreland S (1995) J Med Chem 38:119

    Article  CAS  Google Scholar 

  3. 3.

    Grover GJ, Dzwonczyk S, McMullen DM, Normadinam CS, Sleph PG, Moreland SJ (1995) J Cardiovasc Pharmacol 26:289

    Article  CAS  Google Scholar 

  4. 4.

    Snider BB, Chen J, Patil AD, Freyer A (1996) Tetrahedron Lett 37:6977

    Article  CAS  Google Scholar 

  5. 5.

    Singh K, Singh J, Deb PK, Singh H (1999) Tetrahedron 55:12873

    Article  CAS  Google Scholar 

  6. 6.

    Fu NY, Yuan YF, Cao Z, Wang SW, Wang JT, Peppe C (2002) Tetrahedron 58:4801

    Article  CAS  Google Scholar 

  7. 7.

    Patil AD, Kumar NV, Kokke WC, Bean MF, Freyer AJ, Debrosse C, Mai S, Truneh A, Faulkner DJ, Carte B, Breen AL, Hertzberg RP, Johnson RK, Westly JW, Ports BCM (1995) J Org Chem 60:1182

    Article  CAS  Google Scholar 

  8. 8.

    Ohtani K, Kusumi T, Kakisawa H, Kashman Y, Hirsh S (1992) J Am Chem Soc 114:8472

    Article  CAS  Google Scholar 

  9. 9.

    Overman LE, Rabinowitz MH, Renhowe PA (1995) J Am Chem Soc 117:2657

    Article  CAS  Google Scholar 

  10. 10.

    Jin T, Zhang S, Li T (2002) Synth Commun 32:1847

    Article  CAS  Google Scholar 

  11. 11.

    Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA (2003) Tetrahedron Lett 44:2889

  12. 12.

    Tu S, Fang F, Zhu S, Li T, Zhang X, Zhuang Q (2004) Synlett 537

  13. 13.

    Adibi H, Samimi HA, Beygzadeh M (2007) Catal Commun 8:2119

    Article  CAS  Google Scholar 

  14. 14.

    Hu EH, Sidler DR, Dolling UH (1998) J Org Chem 63:3454

    Article  CAS  Google Scholar 

  15. 15.

    Ma Y, Qian C, Wang L, Yang M (2000) J Org Chem 65:3864

    Article  CAS  Google Scholar 

  16. 16.

    Lu J, Bai Y (2002) Synthesis 466

  17. 17.

    Debache A, Amimour M, Belfaitah A, Rhouati S, Carboni B (2008) Tetrahedron Lett 49:6119

    Article  CAS  Google Scholar 

  18. 18.

    Litvic M, Vecenaj I, Ladisic ZM, Lovric M, Vinkovic V, Litvic MF (2010) Tetrahedron 66:3463

    Article  CAS  Google Scholar 

  19. 19.

    Khrustalev DP (2009) Russ J Gen Chem 79:164

    Article  CAS  Google Scholar 

  20. 20.

    Yadav JS, Reddy BVS, Reddy KB, Raj KS, Prasad AR (2001) J Chem Soc Perkin Trans 1:1939

    Article  Google Scholar 

  21. 21.

    Ding D, Zhao C (2010) Eur J Org Chem 20:3802

    Article  Google Scholar 

  22. 22.

    Fang D, Zhang D, Liu Z (2010) Monatsh Chem 141:419

    Article  CAS  Google Scholar 

  23. 23.

    Sheykhan M, Mamani L, Ebrahimi A, Heydari A (2011) J Mol Catal A: Chem 335:253

    Article  CAS  Google Scholar 

  24. 24.

    Kiasat AR, Nazari S (2012) J Mol Catal A: Chem 365:80

    Article  CAS  Google Scholar 

  25. 25.

    Kiasat AR, Nazari S (2013) J Incl Phenom Macrocycl Chem 76:363

    Article  CAS  Google Scholar 

  26. 26.

    Pfeifer A, Zimmermann K, Plank C (2012) Pharm Res 29:1161

    Article  CAS  Google Scholar 

  27. 27.

    Kassaee MZ, Masrouri H, Movahedi F (2010) Monatsh Chem 141:317

    Article  CAS  Google Scholar 

  28. 28.

    Can K, Ozmen M, Ersoz M (2009) Colloids Surf B 71:154

    Article  CAS  Google Scholar 

  29. 29.

    Kassaee MZ, Masrouri H, Movahedi F (2011) Appl Catal A 395:28

    Article  CAS  Google Scholar 

  30. 30.

    Stevens PD, Fan J, Gardimalla HMR, Yen M, Gao Y (2005) Org Lett 7:2085

    Article  CAS  Google Scholar 

  31. 31.

    Yoon TJ, Kim JI, Lee JK (2003) Inorg Chim Acta 345:228

    Article  CAS  Google Scholar 

  32. 32.

    Su KM, Pan TY, Zhang YL (2002) The Analytic Method of Spectrum. East China University of Science & Technology Press, Shanghai, p 100

    Google Scholar 

  33. 33.

    Talaty ER, Raja S, Storhaug VJ, Dolle A, Carper WR (2004) J Phys Chem B 108:13177

    Article  CAS  Google Scholar 

  34. 34.

    Badruddoza AZM, Hidajat K, Uddin MS (2010) J Colloid Interface Sci 346:337

    Article  CAS  Google Scholar 

  35. 35.

    Cornell RM, Schwertmann U (1996) The Iron Oxides. VCH, New York

    Google Scholar 

  36. 36.

    Siddiqui SA, Narkhede UC, Palimkar SS, Daniel T, Lahoti RJ, Srinivasan KV (2005) Tetrahedron 61:3539

    Article  CAS  Google Scholar 

  37. 37.

    Kappe CO (1997) J Org Chem 17:7201

    Article  Google Scholar 

  38. 38.

    Chen WY, Qin SD, Jin JR (2007) Catal Commun 8:123

    Article  CAS  Google Scholar 

  39. 39.

    Suzuki I, Iwata Y, Takeda K (2008) Tetrahedron Lett 49:3238

    Article  CAS  Google Scholar 

  40. 40.

    Shaterian HR, Ranjbar M (2011) J Mol Liq 160:40

    Article  CAS  Google Scholar 

  41. 41.

    Shaabani A, Rahmati A (2005) Catal Lett 100:177

    Article  CAS  Google Scholar 

  42. 42.

    Besoluk S, Kucukislamoglu M, Nebioglu M, Zengin M, Arslan M (2008) J Iran Chem Soc 5:62

    Article  CAS  Google Scholar 

  43. 43.

    Mahdavinia GH, Sepehrian H (2008) Chin Chem Lett 19:1435

    Article  CAS  Google Scholar 

  44. 44.

    Cheng J, Qi DY (2007) Chin Chem Lett 18:647

    Article  Google Scholar 

Download references

Acknowledgments

We are grateful to the Islamic Azad University Sousangerd Branch for supporting this work.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Simin Nazari.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Nazari, S., Saadat, S., Fard, P.K. et al. Imidazole functionalized magnetic Fe3O4 nanoparticles as a novel heterogeneous and efficient catalyst for synthesis of dihydropyrimidinones by Biginelli reaction. Monatsh Chem 144, 1877–1882 (2013). https://doi.org/10.1007/s00706-013-1085-5

Download citation

Keywords

  • Dihydropyrimidinone
  • Biginelli reaction
  • Magnetic nanoparticles
  • Imidazole