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Magnetic mesoporous poly-melamine–formaldehyde: an efficient and recyclable catalyst for straightforward one-pot synthesis of imidazo[1,2-a]pyridines

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Abstract

Magnetically separable mesoporous poly-melamine–formaldehyde nanocomposite (Fe3O4@mPMF) has been synthesized and characterized by FTIR spectroscopy, SEM, XRD spectroscopy and EDS. The magnetically separable Fe3O4@mPMF catalyst had excellent efficiency for the synthesis a wide diversity of imidazo[1,2-a]pyridines by a three-component reaction of a 2-aminopyridine, aldehyde and isocyanide in good-to-excellent yields within a short reaction time, through an environmental friendliness and straightforward procedure. The nanocomposite that is easily recoverable and also found to be reusable can be recovered and reused when the reaction is completed for several times without distinct deterioration in catalytic activity.

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References

  1. A. Alizadeh, Q. Oskueyan, S. Rostamnia, Synthesis 17, 2637–2640 (2007)

    Article  CAS  Google Scholar 

  2. M.A.P. Martins, C.P. Frizzo, D.N. Moreira, N. Zanatta, H.G. Bonacorso, Chem. Rev. 108, 2015 (2008)

    Article  CAS  PubMed  Google Scholar 

  3. A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Mol. Divers. 15, 41–68 (2011)

    Article  CAS  PubMed  Google Scholar 

  4. S. Gupta, M. Lakshman, J. Med. Chem. Sci. 2, 51–54 (2019)

    Google Scholar 

  5. S. Sajjadifar, K. Pal, H. Jabbari, O. Pouralimardan, F. Divsar, S. Mohammadi-Aghdam, I. Amini, H. Hamidi, Chem. Methodol. 3, 226–236 (2019)

    CAS  Google Scholar 

  6. H. Aghahosseini, A. Ramazani, N. Safarvand-Jalayer, Z. Ranjdoost, A. Souldozi, K. Slepokura, T. Lis, Org. Lett. 21, 22–26 (2019)

    Article  CAS  PubMed  Google Scholar 

  7. A.K. Chakraborti, S. Rudrawar, K.B. Jadhav, G. Kaura, S.V. Chankeshwara, Green Chem. 9, 1335 (2007)

    Article  CAS  Google Scholar 

  8. A. Ramazani, Rezaei, Org. Lett. 12, 2852–2855 (2010)

    Article  CAS  PubMed  Google Scholar 

  9. H. Ahankar, A. Ramazani, K. Ślepokura, T. Lis, S.W. Joo, Green Chem. 18, 3582–3593 (2016)

    Article  CAS  Google Scholar 

  10. H.C. Hu, Y.H. Liu, B.L. Li, Z.S. Cui, Z.H. Zhang, RSC Adv. 5, 48675 (2015)

    Article  CAS  Google Scholar 

  11. P.H. Li, B.L. Li, H.C. Hu, X.N. Zhao, Z.H. Zhang, Catal. Commun. 46, 118 (2014)

    Article  CAS  Google Scholar 

  12. I. Yavari, H. Djahaniani, F. Nasiri, Tetrahedron 59, 9409–9412 (2003)

    Article  CAS  Google Scholar 

  13. Z. Arzehgar, S. Sajjadifar, M.H. Fekri, Chem. Methodol. 3, 251–260 (2019)

    CAS  Google Scholar 

  14. A. Ramazani, M. Khoobi, A. Torkaman, F. Zeinali-Nasrabadi, H. Forootanfar, M. Shakibaie, M. Jafari, A. Amiri, S. Emami, M.A. Faramarzi, A. Foroumadi, A. Shafiee, Eur. J. Med. Chem. 78, 151–156 (2014)

    Article  CAS  PubMed  Google Scholar 

  15. H. Aghahosseini, A. Ramazani, K. Ślepokura, T. Lis, J. Colloid Interface Sci. 511, 222–232 (2018)

    Article  CAS  PubMed  Google Scholar 

  16. I. Yavari, Ramazani, J. Chem. Res. 382–383 (1996)

  17. R. Motamedi, F. Ebrahimi, G. Rezanejade-Bardijee, Asian J. Green Chem. 3, 22–23 (2019)

    Google Scholar 

  18. Z. Arzehgar, S. Sajjadifar, H. Arandiyan, Asian J. Green Chem. 3, 43–52 (2019)

    Google Scholar 

  19. A. Shaabani, E. Soleimani, A. Maleki, Tetrahedron Lett. 47, 3031–3034 (2007)

    Article  CAS  Google Scholar 

  20. E. Ruijter, R. Scheffelaar, R.V.A. Orru, Angew. Chem. Int. Ed. 50, 6234 (2011)

    Article  CAS  Google Scholar 

  21. B.B. Toure, D.G. Hall, Chem. Rev. 109, 4439 (2009)

    Article  CAS  PubMed  Google Scholar 

  22. A. Shaabani, A. Maleki, Appl. Catal. A Gen. 331, 149–151 (2007)

    Article  CAS  Google Scholar 

  23. A. Shaabani, A. Maleki, J. Moghimi-Rad, J. Org. Chem. 72, 6309–6311 (2007)

    Article  CAS  PubMed  Google Scholar 

  24. A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, 316831 (2000)

    Article  Google Scholar 

  25. J. Zhu, Eur. J. Org. Chem. 1133 (2007)

  26. H. Bienayme, K. Bouzid, Angew. Chem. Int. Ed. 37, 2234 (1998)

    Article  CAS  Google Scholar 

  27. N. Devi, R.K. Rawal, V. Singh, Tetrahedron 71, 183 (2015)

    Article  CAS  Google Scholar 

  28. S. Rostamnia, A. Hassankhani, RSC Adv. 3, 18626 (2013)

    Article  CAS  Google Scholar 

  29. S. Rostamnia, K. Lamei, M. Mohammadquli, M. Sheykhan, A. Heydari, Tetrahedron Lett. 53, 5257–5260 (2012)

    Article  CAS  Google Scholar 

  30. S. Vidyacharan, A.H. Shinde, D.S. Sharada, Green Chem. 16, 1168 (2014)

    Article  CAS  Google Scholar 

  31. J. Lu, X.T. Li, E.Q. Ma, L.P. Mo, Z.H. Zhang, Chem. Catal. Chem. 6, 2854 (2014)

    CAS  Google Scholar 

  32. S. Swami, N. Devi, A. Agarwala, V. Singh, R. Shrivastava, Tetrahedron Lett. 57, 1346 (2016)

    Article  CAS  Google Scholar 

  33. M. Adib, M. Mahdavi, M.A. Noghani, P. Mirzaei, Tetrahedron Lett. 48, 7263 (2007)

    Article  CAS  Google Scholar 

  34. M. Zhang, J. Lu, J.N. Zhang, Z.H. Zhang, Catal. Commun. 78, 26 (2016)

    Article  CAS  Google Scholar 

  35. E. Gross, J.H. Liu, F.D. Toste, G.A. Somorjai, Nat. Chem. 4, 947 (2012)

    Article  CAS  PubMed  Google Scholar 

  36. G. Kyriakou, M.B. Boucher, A.D. Jewell, E.A. Lewis, T.J. Lawton, A.E. Baber, Science 335, 1209 (2012)

    Article  CAS  PubMed  Google Scholar 

  37. M. Jakuttis, A. Schönweiz, S. Werner, R. Franke, K.D. Wiese, M. Haumann, P. Wasserscheid, Angew. Chem. Int. Ed. 50, 4492 (2011)

    Article  CAS  Google Scholar 

  38. K.S. Palla, T.J. Hurlburt, A.M. Buyanin, G.A. Somorjai, M.B. Francis, J. Am. Chem. Soc. 139, 1967 (2017)

    Article  CAS  PubMed  Google Scholar 

  39. P. Puthiaraj, Y. Lee, S. Zhang, W.S. Ahn, J. Mater. Chem. A 4, 16288 (2016)

    Article  CAS  Google Scholar 

  40. T. Blasco, Chem. Soc. Rev. 39, 4685 (2010)

    Article  CAS  PubMed  Google Scholar 

  41. D. Schwarz, J. Weber, Polymer 155, 83 (2018)

    Article  CAS  Google Scholar 

  42. D. Schwarz, J. Weber, Macromol. Mater. Eng. 300, 531 (2015)

    Article  CAS  Google Scholar 

  43. D. Yang, P. Liu, N. Zhang, J. You, H. Wang, ChemCatChem 6, 3434 (2014)

    Article  CAS  Google Scholar 

  44. R.A. Molla, M.A. Iqubal, K. Ghosh, S.M. Kamaluddin, RSC Adv. 4, 48177 (2014)

    Article  CAS  Google Scholar 

  45. M.X. Tan, Y.N. Sum, J.Y. Ying, Y. Zhang, Energy Environ. Sci. 6, 3254 (2013)

    Article  CAS  Google Scholar 

  46. M.X. Tan, Y. Zhang, J.Y. Ying, Chemsuschem 6, 1186 (2013)

    Article  CAS  PubMed  Google Scholar 

  47. M.X. Tan, L. Gu, N. Li, J.Y. Ying, Y. Zhang, Green Chem. 15, 1127 (2013)

    Article  CAS  Google Scholar 

  48. Y. Song, R. Ma, C. Jiao, L. Hao, C. Wang, Q. Wu, Z. Wang, Microchim. Acta 185, 19 (2018)

    Article  CAS  Google Scholar 

  49. N. Azizi, F. Ebrahimi, E. Aakbari, F. Aryanasab, M.R. Saidi, Synlett 2797 (2007)

  50. N. Azizi, A. Khajeh-Amiri, H. Ghafuri, M. Bolourtchian, M.R. Saidi, Synlett 2245 (2009)

  51. B. Mirmashhori, N. Azizi, M.R. Saidi, J. Mol. Catal. A Chem. 247, 159 (2006)

    Article  CAS  Google Scholar 

  52. N. Azizi, Z. Manocheri, Res. Chem. Intermed. 38, 1495 (2012)

    Article  CAS  Google Scholar 

  53. M. Bolourtchian, M.M. Hashemi, Monatshefte fur Chemie 140, 1471 (2009)

    Article  CAS  Google Scholar 

  54. T. Sanaeishoar, H. Tavakkoli, F. Mohave, Appl. Catal. A 470, 56–62 (2014)

    Article  CAS  Google Scholar 

  55. M.L. Bode, D. Gravestock, S.S. Moleele, C.W. Westhuyzen, S.C. Pelly, Bioorg. Med. Chem. 19, 4227–4237 (2011)

    Article  CAS  PubMed  Google Scholar 

  56. D.B. Salunke, E. Yoo, N.M. Shukla, R. Balakrishna, S.S. Malladi, V.W. Day, X. Wang, J. Med. Chem. 55, 8137–8151 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  57. A. Shaabani, E. Soleimani, A. Maleki, J. Moghimi-Rad, Synth. Commun. 38, 1090–1095 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The financial support of this work provided by Chemistry and Chemical Engineering Research Center of Iran and Science and Research Branch of Islamic Azad University is gratefully appreciated.

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Correspondence to Najmedin Azizi.

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Heydari, M., Azizi, N., Mirjafari, Z. et al. Magnetic mesoporous poly-melamine–formaldehyde: an efficient and recyclable catalyst for straightforward one-pot synthesis of imidazo[1,2-a]pyridines. J IRAN CHEM SOC 16, 2357–2363 (2019). https://doi.org/10.1007/s13738-019-01705-3

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  • DOI: https://doi.org/10.1007/s13738-019-01705-3

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