Advertisement

New magnetic nanocatalyst containing a bis-dicationic ionic liquid framework for Knoevenagel condensation reaction

  • Reyhaneh Karimi-Chayjani
  • Nader Daneshvar
  • Farhad ShiriniEmail author
  • Hassan Tajik
Article

Abstract

Bis[(3-aminopropyl)triethoxysilane]dichloride immobilized on magnetic nano-γ-Fe2O3@SiO2 has been prepared. After characterization, the reagent was used for efficient promotion of the Knoevenagel reaction, achieving high reaction rates and yields. Also, the recovery and reusability of the catalyst were excellent for the studied reaction.

Keywords

Bis-dicationic magnetic nanoparticles Nano-γ-Fe2O3 Arylidene malononitriles Ethyl-3-aryl-2-cyanoacrylates Water-mediated reaction 

Notes

Acknowledgements

We are grateful to the Research Council of the University of Guilan for partial support of this research.

References

  1. 1.
    W. Wu, Q. He, C. Jiang, Nanoscale Res. Lett. 3, 397 (2008)CrossRefGoogle Scholar
  2. 2.
    M. Colombo, S. Carregal-Romero, M.F. Casula, L. Gutiérrez, M.P. Morales, I.B. Böhm, J.T. Heverhagen, D. Prosperi, W.J. Parak, Chem. Soc. Rev. 41, 4306 (2012)CrossRefGoogle Scholar
  3. 3.
    J.B. Haun, T.J. Yoon, H. Lee, R. Weissleder, WIREs Nanomed. Nanobiotechnol. 2, 291 (2010)CrossRefGoogle Scholar
  4. 4.
    Z. Hamidi, M.A.K. Zarchi, Res. Chem. Intermed. 44, 6995 (2018)CrossRefGoogle Scholar
  5. 5.
    M.N. Chen, L.P. Mo, Z.S. Cui, Z.H. Zhang, Curr. Opin. Green Sustain. Chem. 15, 27 (2019)CrossRefGoogle Scholar
  6. 6.
    D.K. Kim, M. Mikhaylova, F.H. Wang, J. Kehr, B. Bjelke, Y. Zhang, M. Muhammed, Chem. Mater. 15, 4343 (2003)CrossRefGoogle Scholar
  7. 7.
    X.Q. Xu, H. Shen, J.R. Xu, M.Q. Xie, X.J. Li, Appl. Surf. Sci. 253, 2158 (2006)CrossRefGoogle Scholar
  8. 8.
    Z. Rezayati Zad, S.S. Hosseiny Davarani, A. Taheri, Y. Bide, J. Mol. Liq. 253, 233 (2018)CrossRefGoogle Scholar
  9. 9.
    J. Guo, W. Yang, C. Wang, J. He, J. Chen, Chem. Mater. 18, 5554 (2006)CrossRefGoogle Scholar
  10. 10.
    Y. Zhou, Z. Tang, C. Shi, S. Shi, Z. Qian, S. Zhou, J. Mater. Sci. Mater. Med. 23, 2697 (2012)CrossRefGoogle Scholar
  11. 11.
    G. Ruiz, M. Salas, Y. Calero, A. Hernández, F. Herranz, S. Veintemillas-Verdaguer, E. Martínez, D.F. Barber, M.P. Morales, Acta Biomater. 9, 6421 (2013)CrossRefGoogle Scholar
  12. 12.
    J. Sheng, H. Tong, H. Xu, C. Tang, Catal. Surv. Asia 20, 167 (2016)CrossRefGoogle Scholar
  13. 13.
    F. Bao, J.L. Yao, R.A. Gu, Langmuir 25, 10782 (2009)CrossRefGoogle Scholar
  14. 14.
    M. Namvar-Mahboub, E. Khodeir, A. Karimian, Res. Chem. Intermed. 44, 6877 (2018)CrossRefGoogle Scholar
  15. 15.
    M. Zhang, Y.H. Liu, Z.R. Shang, H.C. Hu, Z.H. Zhang, Catal. Commun. 88, 39 (2017)CrossRefGoogle Scholar
  16. 16.
    M. Zhang, P. Liu, Y. Liu, Z.R. Shang, H.C. Hu, Z.H. Zhang, RSC Adv. 6, 106160 (2016)CrossRefGoogle Scholar
  17. 17.
    A. Kiasat, J. Davarpanah, Res. Chem. Intermed. 41, 2991 (2015)CrossRefGoogle Scholar
  18. 18.
    U. Schwertmann, R.M. Cornell, Iron Oxides in the Laboratory: Preparation and Characterization (Wiley, Hoboken, 2008)Google Scholar
  19. 19.
    Y.A. Barnakov, M.H. Yu, Z. Rosenzweig, Langmuir 21, 7524 (2005)CrossRefGoogle Scholar
  20. 20.
    S. Dehghan, B. Kakavandi, R. Rezaei Kalantary, J. Mol. Liq. 44, 6591 (2018)Google Scholar
  21. 21.
    L. Zhu, Y. Liu, J. Chen, Ind. Eng. Chem. Res. 48, 3261 (2009)CrossRefGoogle Scholar
  22. 22.
    A. Ghorbani-Choghamarani, Z. Taherinia, M. Nikoorazm, Res. Chem. Intermed. 44, 6591 (2018)CrossRefGoogle Scholar
  23. 23.
    V.N. Mahire, G.P. Patil, A.B. Deore, P.G. Chavan, H.D. Jirimali, P.P. Mahulikar, Res. Chem. Intermed. 44, 5801 (2018)CrossRefGoogle Scholar
  24. 24.
    B.M. Choudary, M. Lakshmi Kantam, V. Neeraja, K. Koteswara Rao, F. Figueras, L. Delmotte, Green Chem. 3, 257 (2001)CrossRefGoogle Scholar
  25. 25.
    A. Dandia, V. Parewa, A.K. Jain, K.S. Rathore, Green Chem. 13, 2135 (2011)CrossRefGoogle Scholar
  26. 26.
    B.C. Hong, N.S. Dange, C.F. Ding, J.H. Liao, Org. Lett. 14, 448 (2012)CrossRefGoogle Scholar
  27. 27.
    H. Yan, H.Y. Zhang, L. Wang, Y. Zhang, J. Zhao, React. Kinet. Mech. Catal. 125, 789 (2018)CrossRefGoogle Scholar
  28. 28.
    N. Mase, T. Horibe, Org. Lett. 15, 1854 (2013)CrossRefGoogle Scholar
  29. 29.
    M. Abass, E.A. Mohamed, M.M. Ismail, A.S. Mayas, J. Mex. Chem. Soc. 55, 224 (2011)Google Scholar
  30. 30.
    M.S. Hoekstra, D.M. Sobieray, M.A. Schwindt, T.A. Mulhern, T.M. Grote, B.K. Huckabee, V.S. Hendrickson, L.C. Franklin, E.J. Granger, G.L. Karrick, Org. Process Res. Dev. 1, 26 (1997)CrossRefGoogle Scholar
  31. 31.
    B.N. Roy, G.P. Singh, P.S. Lathi, M.K. Agrawal, R. Mitra, V.S. Pise, Indian J. Chem. 51, 1470 (2012)Google Scholar
  32. 32.
    G. Srikanth, U.K. Ray, D.V.N.S. Rao, P.B. Gupta, P. Lavanya, A. Islam, Synth. Commun. 49, 1359 (2012)CrossRefGoogle Scholar
  33. 33.
    A. Ying, L. Wang, F. Qiu, H. Hu, J. Yang, C. R. Chim. 18, 223 (2015)CrossRefGoogle Scholar
  34. 34.
    M. Gilanizadeh, B. Zeynizadeh, Res. Chem. Intermed. 44, 6053 (2018)CrossRefGoogle Scholar
  35. 35.
    R. Vaid, M. Gupta, Monatsh. Chem. 146, 645 (2015)CrossRefGoogle Scholar
  36. 36.
    R.G. Chaudhary, J.A. Tanna, N.V. Gandhare, A.R. Rai, H.D. Juneja, Adv. Mater. Lett. 6, 990 (2015)CrossRefGoogle Scholar
  37. 37.
    P. Ossowicz, Z. Rozwadowski, M. Gano, E. Janus, Pol. J. Chem. 18, 90 (2016)CrossRefGoogle Scholar
  38. 38.
    F. Shirini, N. Daneshvar, RSC Adv. 6, 110190 (2016)CrossRefGoogle Scholar
  39. 39.
    P. Kaliyan, S. Matam, S. Perumal Muthu, Asian J. Green Chem. (2019)Google Scholar
  40. 40.
    A. Bamoniri, N. Moshtael-Arani, RSC Adv. 5, 16911 (2015)CrossRefGoogle Scholar
  41. 41.
    M. Jafarpour, A. Rezaeifard, V. Yasinzadeh, H. Kargar, RSC Adv. 5, 38460 (2015)CrossRefGoogle Scholar
  42. 42.
    W. Stöber, A. Fink, E. Bohn, J. Colloid Interface Sci. 26, 62 (1968)CrossRefGoogle Scholar
  43. 43.
    N. Daneshvar, F. Shirini, M.S.N. Langarudi, R. Karimi-Chayjani, Bioorg. Chem. 77, 68 (2018)CrossRefGoogle Scholar
  44. 44.
    N. Daneshvar, M. Nasiri, M. Shirzad, M.S.N. Langarudi, F. Shirini, H. Tajik, New J. Chem. 42, 9744 (2018)CrossRefGoogle Scholar
  45. 45.
    F. Shirini, M.S.N. Langarudi, N. Daneshvar, M. Mashhadinezhad, N. Nabinia, J. Mol. Liq. 243, 302 (2017)CrossRefGoogle Scholar
  46. 46.
    F. Shirini, M.S.N. Langarudi, N. Daneshvar, J. Mol. Liq. 234, 268 (2017)CrossRefGoogle Scholar
  47. 47.
    S. Darvishzad, N. Daneshvar, F. Shirini, H. Tajik, Mol. Struct. (2018)Google Scholar
  48. 48.
    F. Kamali, F. Shirini, New J. Chem. 41, 11778 (2017)CrossRefGoogle Scholar
  49. 49.
    M. Haghighat, F. Shirini, M. Golshekan, J. Mol. Struct. 1171, 168 (2018)CrossRefGoogle Scholar
  50. 50.
    N. Azgomi, M. Mokhtary, J. Mol. Catal. A: Chem. 398, 58 (2015)CrossRefGoogle Scholar
  51. 51.
    C. Zhuo, D. Xian, W. Jian-wei, X. Hui, ISRN Org. Chem. 2011, 1 (2011)CrossRefGoogle Scholar
  52. 52.
    A. Rostami, B. Atashkar, H. Gholami, Catal. Commun. 37, 69 (2013)CrossRefGoogle Scholar
  53. 53.
    Y. Xian-Cao, J. Hong, Y. Wen, Synth. Commun. 42, 309 (2011)Google Scholar
  54. 54.
    D. Xu, Y. Liu, S. Shi, Y. Wang, Green Chem. 12, 514 (2010)CrossRefGoogle Scholar
  55. 55.
    M. Gupta, R. Gupta, M. Anand, Beilstein J. Org. Chem. 5, 1 (2009)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Reyhaneh Karimi-Chayjani
    • 1
  • Nader Daneshvar
    • 1
  • Farhad Shirini
    • 1
    • 2
    Email author
  • Hassan Tajik
    • 1
    • 2
  1. 1.Department of Chemistry, University Campus 2University of GuilanRashtIran
  2. 2.Department of Chemistry, College of SciencesUniversity of GuilanRashtIran

Personalised recommendations