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Unique role of 2-hydroxyethylammonium acetate as an ionic liquid in the synthesis of Fe3O4 magnetic nanoparticles and preparation of pyridine derivatives in the presence of a new magnetically recyclable heterogeneous catalyst

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Abstract

In this paper, 2-hydroxyethylammonium acetate (2-HEAA) was used as the first functionalized ionic liquid for the facile, economical and environmentally friendly synthesis of Fe3O4 nanoparticles by a co-precipitation method. The synthesized Fe3O4 nanoparticles were used as solid material for supporting 2-HEAA (Fe3O4-2-HEAA). The newly prepared Fe3O4-2-HEAA was characterized by TEM, XRD, FT-IR, TGA and elemental analysis and successfully applied as a magnetically recyclable heterogeneous catalyst for the efficient one-pot, three-component synthesis of 2-amino-3,5-dicarbonitrile-6-thio-pyridines. The catalyst was easily separated by an external magnet and reused at least five times without significant degradation in the activity.

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References

  1. A. Kumar, S.S. Pawar, J. Org. Chem. 69, 1419 (2004)

    Article  CAS  Google Scholar 

  2. R.A. Brown, P. Pollet, E. McKoon, C.A. Eckert, C.L. Liotta, P.G. Jessop, J. Am. Chem. Soc. 123, 1254 (2001)

    Article  CAS  Google Scholar 

  3. W. Leitner, Nature. 423, 930 (2003)

    Article  CAS  Google Scholar 

  4. B.C. Ranu, R. Jana, J. Org. Chem. 70, 8621 (2005)

    Article  CAS  Google Scholar 

  5. T. Zhu, D. Jiang, B. Wang, L. Han, J. Liu, J. Huang, D. Zhang, Sun, Green Chem. 7, 514 (2005)

    Article  CAS  Google Scholar 

  6. J.P. Hallett, T. Welton, Chem. Rev. 111, 3508 (2011)

    Article  CAS  Google Scholar 

  7. C. Vollmer, Janiak, Coord. Chem. Rev. 255, 2039 (2011)

    Article  CAS  Google Scholar 

  8. Z. Li, Z. Jia, Y. Luan, T. Mu, Curr. Opin. Solid State Mater. Sci. 12, 1 (2008)

    Article  Google Scholar 

  9. Y. Wang, H. Yang, Chem. Eng. J. 147, 71 (2009)

    Article  CAS  Google Scholar 

  10. S.-W. Cao, Y.-J. Zhu, G.-F. Cheng, Y.-H. Huang, J. Hazard. Mater. 171, 431 (2009)

    Article  CAS  Google Scholar 

  11. Z. Ma, J. Yu, S. Dai, Adv. Mater. 22, 261 (2010)

    Article  CAS  Google Scholar 

  12. J. Dupont, J.D. Scholten, Chem. Soc. Rev. 39, 1780 (2010)

    Article  CAS  Google Scholar 

  13. V.I. Parvulescu, C. Hardacre, Chem. Rev. 107, 2615 (2007)

    Article  CAS  Google Scholar 

  14. S.W. Tang, A.M. Scurto, B. Subramaniam, J. Catal. 268, 243 (2009)

    Article  CAS  Google Scholar 

  15. N. Yan, Y. Yuan, R. Dykeman, Y. Kou, P.J. Dyson, Angew. Chem. 122, 5681 (2010)

    Article  Google Scholar 

  16. S. Sobhani, M. Honarmand, J. Iran. Chem. Soc. 9, 661 (2012)

    Article  CAS  Google Scholar 

  17. S. Sobhani, M. Honarmand, Synlett. 24, 236 (2013)

    Article  CAS  Google Scholar 

  18. T. Selvam, A. Machoke, W. Schwieger, Appl. Catal. A 445, 92 (2012)

    Article  Google Scholar 

  19. Y.-H. Kim, S. Shin, H.-J. Yoon, J.W. Kim, J.K. Cho, Y.-S. Lee, Catal. Commun. 40, 18 (2013)

    Article  CAS  Google Scholar 

  20. J. Miao, H. Wan, Y. Shao, G. Guan, B. Xu, J. Mol. Catal. A Chem. 348, 77 (2011)

    Article  CAS  Google Scholar 

  21. X. Zheng, S. Luo, L. Zhang, J.-P. Cheng, Green Chem. 11, 455 (2009)

    Article  CAS  Google Scholar 

  22. S. Azad, B.B.F. Mirjalili, RSC Adv. 6, 96928 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. J. Li, F. Wang, H. Chen, Jing, RSC Adv. 7, 4237 (2017)

    Article  CAS  Google Scholar 

  25. X. Zheng, L. Zhang, J. Li, S. Luo, J.-P. Cheng, Chem. Commun. 47, 12325 (2011)

    Article  CAS  Google Scholar 

  26. R. Mrówczyński, A. Nan, J. Liebscher, RSC Adv. 4, 5927 (2014)

    Article  Google Scholar 

  27. K. Guo, R. Mutter, W. Heal, T.R. Reddy, H. Cope, S. Pratt, M.J. Thompson, B. Chen, Eur. J. Med. Chem. 43, 93 (2008)

    Article  CAS  Google Scholar 

  28. B.C. May, J.A. Zorn, J. Witkop, J. Sherrill, A.C. Wallace, G. Legname, S.B. Prusiner, F.E. Cohen, J. Med. Chem. 50, 65 (2007)

    Article  CAS  Google Scholar 

  29. M.T. Cocco, C. Congiu, V. Lilliu, V. Onnis, Eur. J. Med. Chem. 40, 1365 (2005)

    Article  CAS  Google Scholar 

  30. S. Ray, P. Das, A. Bhaumik, M. Pramanik, C. Mukhopadhyay, Recycl. Catal. 1, 34 (2012)

    Google Scholar 

  31. M.N. Khan, S. Pal, T. Parvin, L.H. Choudhury, RSC Adv. 2, 12305 (2012)

    Article  CAS  Google Scholar 

  32. M. Sridhar, B.C. Ramanaiah, C. Narsaiah, B. Mahesh, M. Kumaraswamy, K.K. Mallu, V.M. Ankathi, P.S. Rao, Tetrahedron Lett. 50, 3897 (2009)

    Article  CAS  Google Scholar 

  33. S. Mishra, R. Ghosh, Synth. Commun. 42, 2229 (2012)

    Article  CAS  Google Scholar 

  34. P.V. Shinde, V.B. Labade, B.B. Shingate, M.S. Shingare, J. Mol. Catal. A Chem. 336, 100 (2011)

    Article  CAS  Google Scholar 

  35. M.A. Ghasemzadeh, Acta Chim. Slov. 59, 697 (2012)

    PubMed  Google Scholar 

  36. J. Safaei-Ghomi, M.A. Ghasemzadeh, J. Sulfur Chem. 34, 233 (2013)

    Article  CAS  Google Scholar 

  37. M.L. Kantam, K. Mahendar, S. Bhargava, J. Chem. Sci. 122, 63 (2010)

    Article  CAS  Google Scholar 

  38. S. Banerjee, G. Sereda, Tetrahedron Lett. 50, 6959 (2009)

    Article  CAS  Google Scholar 

  39. P. Davoodnia, H. Attar, A. Eshghi, N. Morsali, A. Tavakoli-Hoseini, Tavakoli-Nishaburi, Asian J. Chem. 23, 1273 (2011)

    CAS  Google Scholar 

  40. B.C. Ranu, R. Jana, S. Sowmiah, J. Org. Chem. 72, 3152 (2007)

    Article  CAS  Google Scholar 

  41. S. Sobhani, M. Honarmand, C. R. Chim. 16, 279 (2013)

    Article  CAS  Google Scholar 

  42. S. Sobhani, M. Honarmand, Appl. Catal. A 467, 456 (2013)

    Article  CAS  Google Scholar 

  43. S. Sobhani, Z. Pakdin-Parizi, R. Nasseri, J. Chem. Sci. 125, 975 (2013)

    Article  CAS  Google Scholar 

  44. S. Sobhani, M.S. Ghasemzadeh, M. Honarmand, F. Zarifi, RSC Adv. 4, 44166 (2014)

    Article  CAS  Google Scholar 

  45. S. Sobhani, F. Zarifi, RSC Adv. 5, 96532 (2015)

    Article  CAS  Google Scholar 

  46. S. Sobhani, F. Zarifi, J. Skibsted, ChemistrySelect. 1, 2945 (2016)

    Article  CAS  Google Scholar 

  47. S. Sobhani, F. Zarifi, J. Skibsted, New J. Chem. 41, 6219 (2017)

    Article  CAS  Google Scholar 

  48. S. Sobhani, F. Zarifi, J. Skibsted, ACS Sustain. Chem. Eng. 5, 4598 (2017)

    Article  CAS  Google Scholar 

  49. S. Sobhani, F. Khakzad, Appl. Organomet. Chem. 31, e3877 (2017)

    Article  Google Scholar 

  50. A. Yue, Y. Mao, M. Wei, Lü, Catal. Commun. 9, 1571 (2008)

    Article  CAS  Google Scholar 

  51. S. Sobhani, M. Honarmand, Catal. Lett. 143, 476 (2013)

    Article  CAS  Google Scholar 

  52. S. Sobhani, M. Honarmand, Can. J. Chem. 90, 798 (2012)

    Article  CAS  Google Scholar 

  53. C.-M. Lee, H.-J. Jeong, S.T. Lim, M.-H. Sohn, D.W. Kim, ACS Appl. Mater. Interfaces. 2, 756 (2010)

    Article  CAS  Google Scholar 

  54. Y. Wang, S. Maksimuk, R. Shen, H. Yang, Green Chem. 9, 1051 (2007)

    Article  Google Scholar 

  55. J. Hu, X. Hu, A. Chen, S. Zhao, J. Alloys Compd. 603, 1 (2014)

    Article  CAS  Google Scholar 

  56. F.C. Oliveira, L.M. Rossi, R.F. Jardim, J.C. Rubim, J. Phys. Chem. C 113, 8566 (2009)

    Article  CAS  Google Scholar 

  57. S.-W. Cao, Y.-J. Zhu, Acta Mater. 57, 2154 (2009)

    Article  CAS  Google Scholar 

  58. K.N. Singh, S.K. Singh, Arkivoc. xiii, 153 (2009)

    Google Scholar 

  59. R. Mamgain, R. Singh, D.S. Rawat, J. Heterocycl. Chem. 46, 69 (2009)

    Article  CAS  Google Scholar 

  60. N.M. Evdokimov, A.S. Kireev, A.A. Yakovenko, M.Y. Antipin, I.V. Magedov, A. Kornienko, J. Org. Chem. 72, 3443 (2007)

    Article  CAS  Google Scholar 

  61. N.M. Evdokimov, I.V. Magedov, A.S. Kireev, A. Kornienko, Org. Lett. 8, 899 (2006)

    Article  CAS  Google Scholar 

  62. Z.Q. Wang, Z.M. Ge, T.M. Cheng, R.T. Li, Synlett 2009, 2020 (2009)

    Article  Google Scholar 

  63. A. Shaikh, G. Shaikh, Nazeruddin, J. Chem. Pharm. Res. 4, 4953 (2012)

    CAS  Google Scholar 

  64. V. Kamble, S. Atkore, P. Pisal, M. Sadaf, R.V. Thakre, Iran. Chem. Commun. 4, 186 (2016)

    CAS  Google Scholar 

  65. M.S. Su, X.J. Ji, B.B. Zhao, M. Tian, J.J. Ma, J. Chem. Soc. Pak. 37, 1130 (2015)

    CAS  Google Scholar 

  66. U.V. Desai, M.A. Kulkarni, K.S. Pandit, A.M. Kulkarni, P.P. Wadgaonkar, Green Chem. Lett. Rev. 7, 228 (2014)

    Article  Google Scholar 

  67. M. Thimmaiah, P. Li, S. Regati, B. Chen, J.C.-G. Zhao, Tetrahedron Lett. 53, 4870 (2012)

    Article  CAS  Google Scholar 

  68. S. Takale, J. Patil, V. Padalkar, R. Pisal, A. Chaskar, J. Braz. Chem. Soc. 23, 966 (2012)

    Article  CAS  Google Scholar 

  69. M.R.P. Heravi, F. Fakhr, Tetrahedron Lett. 52, 6779 (2011)

    Article  Google Scholar 

  70. J.B. Gujar, M.A. Chaudhari, D.S. Kawade, M.S. Shingare, Tetrahedron Lett. 55, 6939 (2014)

    Article  CAS  Google Scholar 

  71. P.V. Shinde, B.B. Shingate, M.S. Shingare, Chin. J. Chem. 29, 1049 (2011)

    Article  CAS  Google Scholar 

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Acknowledgements

Financial support of this project by University of Birjand Research Council is appreciated.

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Authors and Affiliations

  1. Department of Chemistry, College of Sciences, University of Birjand, Birjand, Iran

    Sara Sobhani, Fatemeh Nasseri & Farzaneh Zarifi

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  1. Sara Sobhani
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  2. Fatemeh Nasseri
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Correspondence to Sara Sobhani.

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Sobhani, S., Nasseri, F. & Zarifi, F. Unique role of 2-hydroxyethylammonium acetate as an ionic liquid in the synthesis of Fe3O4 magnetic nanoparticles and preparation of pyridine derivatives in the presence of a new magnetically recyclable heterogeneous catalyst. J IRAN CHEM SOC 15, 2721–2732 (2018). https://doi.org/10.1007/s13738-018-1460-6

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