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Journal of the Iranian Chemical Society

, Volume 16, Issue 2, pp 341–354 | Cite as

s-Triazinium-based ionic liquid immobilized on silica-coated Fe3O4 magnetic nanoparticles: an efficient and magnetically separable heterogeneous catalyst for synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile derivatives for antioxidant and antifungal evaluation studies

  • Davood AzarifarEmail author
  • Hakimeh Ebrahimiasl
  • Roya Karamian
  • Masoumeh Ahmadi-Khoei
Original Paper
  • 17 Downloads

Abstract

We have described a new method to heterogenize s-triazine catalyst by easy preparation of ionic liquid-based s-triazine-immobilized silica-coated Fe3O4 magnetic nanoparticles [Fe3O4@SiO2-s-triazinium chloride]. The structure of the newly prepared nanoparticles was characterized by Fourier transform infrared, X-ray powder diffraction, scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray method, vibrating sample magnetometery and thermo-gravimetric analysis. These nanoparticles were identified as an efficient catalyst for one-pot three-component synthesis of 4,8-dihydropyrano[3,2-b]pyran derivatives in excellent yields. The catalyst was easily separated by magnetic decantation, and the recovered nanoparticles were reused for four fresh runs without any significant loss of catalytic activity. The synthesized dihydropyrano[3,2-b]pyrans were evaluated for their antioxidant and antifungal activities and found they are relatively active.

Keywords

Immobilized ionic liquid s-Triazine-functionalized silica-coated Fe3O4 magnetic nanoparticles 4,8-Dihydropyrano[3,2-b]pyrans One-pot three-component reaction Magnetic catalyst Antioxidant Antifungal 

Notes

Acknowledgements

The authors wish to thank the Research Council of Bu-Ali Sina University for financial support to carry out this research. Also, Mr. Jamshid Rakhtshah from Tabriz University is greatly acknowledged for his generous contribution of some chemical materials utilized in this research.

References

  1. 1.
    M.J. Earle, K.R. Seddon, Pure Appl. Chem. 72, 1391 (2000)CrossRefGoogle Scholar
  2. 2.
    S.-G. Lee, Chem. Commun. 10, 1049 (2006)CrossRefGoogle Scholar
  3. 3.
    J.H. Davis, James Jr., Chem. Lett. 33, 1072 (2004)CrossRefGoogle Scholar
  4. 4.
    C. Paun, J. Barklie, P. Goodrich, H. Gunaratne, A. McKeown, V. Parvulescu, C. Hardacre, J. Mol. Catal. A Chem. 269, 64 (2007)CrossRefGoogle Scholar
  5. 5.
    B.C. Ranu, S. Banerjee, Org. Lett. 7, 3049 (2005)CrossRefGoogle Scholar
  6. 6.
    M.A. Zolfigol, S. Baghery, A.R. Moosavi-Zare, S.M. Vahdat, H. Alinezhad, M. Norouzi, RSC Adv. 4, 57662 (2014)CrossRefGoogle Scholar
  7. 7.
    H. Alinezhad, M. Tajbakhsh, M. Norouzi, S. Baghery, World Appl. Sci. J. 22, 1711 (2013)Google Scholar
  8. 8.
    A.C. Cole, J.L. Jensen, I. Ntai, K.L. Tran, K.J. Weaver, D.C. Forbes, J.H. Davis, J. Am. Chem. Soc. 124, 5962 (2002)CrossRefGoogle Scholar
  9. 9.
    T. Welton, Coord. Chem. Rev. 248, 2459 (2004)CrossRefGoogle Scholar
  10. 10.
    J. Miao, H. Wan, G. Guan, Cat. Commun. 12, 353 (2011)CrossRefGoogle Scholar
  11. 11.
    J. Safari, Z. Zarnegar, Monatsh. Chem. 144, 1389 (2013)CrossRefGoogle Scholar
  12. 12.
    S. Sahoo, P. Kumar, F. Lefebvre, S.B. Halligudi, Appl. Catal. A 354, 17 (2009)CrossRefGoogle Scholar
  13. 13.
    M.H. Valkenberg, C. deCastro, W.F. Hölderich, Green Chem. 4, 88 (2002)CrossRefGoogle Scholar
  14. 14.
    M.H. Valkenberg, C. de Castro, W.F. Hölderich, Top. Catal. 14, 139 (2001)CrossRefGoogle Scholar
  15. 15.
    H. A.Corma, A. Garcı´a, Leyva, Tetrahedron 60, 8553 (2004)CrossRefGoogle Scholar
  16. 16.
    X. Wu, F. Zhao, J.R. Varcoe, A.E. Thumser, C. Avignone-Rossa, R.C. Slade, Bioelectrochemistry 77, 64 (2009)CrossRefGoogle Scholar
  17. 17.
    Z. Zarnegar, J. Safari, New J. Chem. 40, 7986 (2016)CrossRefGoogle Scholar
  18. 18.
    L. Rodríguez-Pérez, E. Teuma, A. Falqui, M. Gómez, P. Serp, Chem. Commun. 35, 4201 (2008)CrossRefGoogle Scholar
  19. 19.
    W.-H. Zhang, P.-P. He, S. Wu, J. Xu, Y. Li, G. Zhang, X.-Y. Wei, Appl. Catal. A Gen. 509, 111 (2016)CrossRefGoogle Scholar
  20. 20.
    W. Zheng, R. Tan, S. Yin, Y. Zhang, G. Zhao, Y. Chen, D. Yin, Catal. Sci. Technol. 5, 2092 (2015)CrossRefGoogle Scholar
  21. 21.
    W. Xie, L. Hu, X. Yang, Ind. Eng. Chem. Res. 54, 1505 (2015)CrossRefGoogle Scholar
  22. 22.
    B. Zou, Y. Hu, L. Jiang, R. Jia, H. Huang, Ind. Eng. Chem. Res. 52, 2844 (2013)CrossRefGoogle Scholar
  23. 23.
    B. Zhen, Q. Jiao, Y. Zhang, Q. Wu, H. Li, Appl. Catal. A Gen. 445, 239 (2012)CrossRefGoogle Scholar
  24. 24.
    Y. Gu, C. Ogawa, S. Kobayashi, Org. Lett. 9, 175 (2007)CrossRefGoogle Scholar
  25. 25.
    H. Hagiwara, Y. Sugawara, K. Isobe, T. Hoshi, T. Suzuki, Org. Lett. 6, 2325 (2004)CrossRefGoogle Scholar
  26. 26.
    C. Yuan, Z. Huang, J. Chen, Catal. Commun. 24, 56 (2012)CrossRefGoogle Scholar
  27. 27.
    P. Wang, H. Liu, J. Niu, R. Li, J. Ma, Catal. Sci. Technol. 4, 1333 (2014)CrossRefGoogle Scholar
  28. 28.
    M.B. Gawande, A.K. Rathi, P.S. Branco, R.S. Varma, Appl. Sci. 3, 656 (2013)CrossRefGoogle Scholar
  29. 29.
    R.B. Nasir Baig, R.S. Varma, Chem. Commun. 49, 752 (2013)CrossRefGoogle Scholar
  30. 30.
    Y. Zhu, L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, N.S. Hosmane, Chem. Catal. Chem. 2, 365 (2010)Google Scholar
  31. 31.
    R. Tayebee, M. Amini, H. Rostamian, A. Aliakbari, Dalton Trans. 43, 1550 (2014)CrossRefGoogle Scholar
  32. 32.
    R. Tayebee, M. Amini, N. Abdollahi, A. Aliakbari, S. Rabiee, H. Ramshini, Appl. Catal. A Gen. 468, 75 (2013)CrossRefGoogle Scholar
  33. 33.
    V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrera, J.M. Basset, Chem. Rev. 111, 3036 (2011)CrossRefGoogle Scholar
  34. 34.
    G.B. Dharma, M.P. Kaushik, A.K. Halve, Tetrahedron Lett. 53, 2741 (2012)CrossRefGoogle Scholar
  35. 35.
    L. Ma’mani, M. Sheykhan, A. Heydari, M. Faraji, Y. Yamini, Appl. Catal. A Gen. 377, 64 (2010)CrossRefGoogle Scholar
  36. 36.
    X. Zheng, S. Liu, L. Zhang, J.P. Cheng, Green Chem. 11, 455 (2009)CrossRefGoogle Scholar
  37. 37.
    Q.M. Kainz, O. Reiser, Acc. Chem. Res. 47, 667 (2014)CrossRefGoogle Scholar
  38. 38.
    D. Guin, B. Baruwati, S.V. Manorama, Org. Lett. 9, 1419 (2007)CrossRefGoogle Scholar
  39. 39.
    B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem. Asian. J. 5, 2318 (2010)CrossRefGoogle Scholar
  40. 40.
    Y. Zou, Y. Hu, H. Liu, D. Shi, ACS Comb. Sci. 14, 38 (2012)CrossRefGoogle Scholar
  41. 41.
    Z. Huang, Y. Hu, Y. Zhou, D. Shi, ACS Comb. Sci. 13, 45 (2011)CrossRefGoogle Scholar
  42. 42.
    C. de Graaff, E. Ruijter, R.V.A. Orru, Chem. Soc. Rev. 41, 3969 (2012)CrossRefGoogle Scholar
  43. 43.
    L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)CrossRefGoogle Scholar
  44. 44.
    W. Kemnitzer, S. Jiang, Y. Wang, S. Kasibhatla, C. Crogan-Grundy, M. Bubenik, D. Labrecque, R. Denis, S. Lamothe, G. Attardo, H. Gourdeau, B. Tseng, J. Drewe, S.X. Cai Bioorg. Med. Chem. Lett. 18, 603 (2008)CrossRefGoogle Scholar
  45. 45.
    N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14, 4792 (2006)CrossRefGoogle Scholar
  46. 46.
    L. Moafi, S. Ahadi, A. Bazgir, Tetrahedron Lett. 51, 6270 (2010)CrossRefGoogle Scholar
  47. 47.
    B.V. Subba Reddy, M. Ramana Reddy, G. Narasimhulu, J.S. Yadav, Tetrahedron Lett. 51, 5677 (2010)CrossRefGoogle Scholar
  48. 48.
    S. Gao, C.H. Tsai, C. Tseng, C.-F. Yao, Tetrahedron 64, 9143 (2008)CrossRefGoogle Scholar
  49. 49.
    M.P. Zhu, I. Kimiaki, Tetrahedron Lett. 38, 5301 (1997)CrossRefGoogle Scholar
  50. 50.
    X. Xiong, M.C. Pirrung, Org. Lett. 10, 1151 (2008)CrossRefGoogle Scholar
  51. 51.
    M. Sefkow, H. Kaatz, Tetrahedron Lett. 40, 6561 (1999)CrossRefGoogle Scholar
  52. 52.
    R.C. Fox, P.D. Taylor, Synth. Commun. 28, 1575 (1998)CrossRefGoogle Scholar
  53. 53.
    J. Safari, S.H. Banitaba, S. Dehghan Khalili, J. Mol. Catal. A Chem. 335, 46 (2011)CrossRefGoogle Scholar
  54. 54.
    D. Ding, C.-G. Zhao, Tetrahedron Lett. 51, 1322 (2010)CrossRefGoogle Scholar
  55. 55.
    S.H. Banitaba, J. Safari, S. Dehghan, Khalili, Ultrason. Sonochem. 20, 401 (2013)CrossRefGoogle Scholar
  56. 56.
    B. Sadeghi, P. Farokhi, S. Hashemian, J. Chem. Res. 38, 54 (2014)CrossRefGoogle Scholar
  57. 57.
    A. Azarifar, R. Nejat-Yami, M. AlKobaisi, D. Azarifar, J. Iran.Chem. Soc. 10, 439 (2013)CrossRefGoogle Scholar
  58. 58.
    D. Azarifar, F. Soleimanei, RSC Adv. 4, 12119 (2014)CrossRefGoogle Scholar
  59. 59.
    D. Azarifar, O. Badalkhani, Y. Abbasi, J. Sulf. Chem. 37, 656 (2016)CrossRefGoogle Scholar
  60. 60.
    D. Azarifar, M. Ghaemi, Appl. Organometal. Chem. 36, 1981 (2017)Google Scholar
  61. 61.
    D. Azarifar, Y. Abbasi, Synth. Commun. 46, 745 (2016)CrossRefGoogle Scholar
  62. 62.
    L. Mensor, F.S. Menezes, G.G. Leitao, A.S. Reis, T.S. Santos, C.S. Coube, Phytother. Res. 15, 127 (2001)CrossRefGoogle Scholar
  63. 63.
    M. Ma, Y. Zhang, W. Yu, H.Y. Shen, H.Q. Zhang, N. Gu, Colloids Surf. A 212, 219 (2003)CrossRefGoogle Scholar
  64. 64.
    W. Stober, A. Fink, E.J. Bohn, J. Colloid Interface Sci. 26, 62 (1968)CrossRefGoogle Scholar
  65. 65.
    T.Z. Yang, C.M. Shen, H.J. Gao, J. Phys. Chem. B 109, 23233 (2005)CrossRefGoogle Scholar
  66. 66.
    X.X. Menga, B.X. Dua, B. Zhaoa, Y.L. Lia, C.F. Chenb, J. Chem. Res. 78, 638 (2013)CrossRefGoogle Scholar
  67. 67.
    J. Mondal, A. Modak, A. Bhaumik, J. Mol. Catal. A Chem. 335, 236 (2011)CrossRefGoogle Scholar
  68. 68.
    R.M. Seabra, P.B. Andrade, P. Valentao, E. Fernandes, F. Carvalho, M.L. Bastos. In: Fingerman, M., Nagabhushanam, R. (eds.) Biomaterials from Aquatic and Terrestrial Organisms, vol 5, p. 115. Science Publishers, Enfield (2006)Google Scholar
  69. 69.
    L. Yu, J. Perret, B. Davy, J. Wilson, C.L. Melby, Food Chem. Toxicol. 67, 2600 (2002)Google Scholar
  70. 70.
    R.L. Prior, X.M. Wu, K. Schaich, J. Agric. Food Chem. 53, 4290 (2005)CrossRefGoogle Scholar
  71. 71.
    A.J. Parr, J.P. Bolwell, J. Sci. Food Agric. 80, 985 (2002)CrossRefGoogle Scholar
  72. 72.
    D. Villano, M.S. Fernandez-Pachon, M.L. Moya, A.M. Troncoso, M.C. Garcia-Parilla, Talanta 71, 230 (2007)CrossRefGoogle Scholar
  73. 73.
    G.N. Agrios, Plant Pathology, 3rd ed, vol 803. Academic Press, Inc., New York (1988)Google Scholar
  74. 74.
    P.R. Larkin, D.R. Fravel. Plant Dis. 82, 1022 (1998)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  • Davood Azarifar
    • 1
    Email author
  • Hakimeh Ebrahimiasl
    • 1
  • Roya Karamian
    • 2
  • Masoumeh Ahmadi-Khoei
    • 2
  1. 1.Department of ChemistryBu-Ali Sina UniversityHamedanIran
  2. 2.Department of Biology, Faculty of ScienceBu-Ali Sina UniversityHamedanIran

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