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Amine-Functionalized Silica-Supported Magnetic Nanoparticles: Preparation, Characterization and Catalytic Performance in the Chromene Synthesis

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Abstract

An efficient, one-pot multicomponent procedure for good to excellent yield preparation of 2-amino-4H-chromene-4-carboxylate and 2-amino-5H-pyrano[3,2-c]chromene-4-carboxylate using Fe3O4@SiO2–NH2 nanoparticles as a facile synthesized, easily recoverable, heterogeneous catalyst was investigated. The amine-functionalized silica-supported magnetic catalyst was characterized successfully by Fourier transforms infrared spectroscopy, scanning electron microscopy and energy-dispersive X-ray spectroscopy analyses. Using ethanol as a green solvent in these multicomponent reactions and no significant decrease in catalytic activity of the nanocatalyst during recovering process are other major points in this worthy chromene derivatives synthesis.

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References

  1. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.-M. Basset, Chem. Rev. 111, 3036–3075 (2011)

    Article  CAS  Google Scholar 

  2. H. Bienayme´, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J 6, 3321–3329 (2000)

    Article  Google Scholar 

  3. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083–3135 (2012)

    Article  Google Scholar 

  4. H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, I. Kianicka, D. Custeau, C. Boudreau, L. Geerts, S.X. Cai, Mol. Cancer Ther. 3, 1375–1384 (2004)

    CAS  Google Scholar 

  5. C.B. Sangani, N.M. Shah, M.P. Patel, R.G. Patel, J. Serbian Chem. Soc. 77, 1165–1174 (2012)

    Article  CAS  Google Scholar 

  6. M. Mladenović, M. Mihailović, D. Bogojević, S. Matić, N. Nićiforović, V. Mihailović, N. Vuković, S. Sukdolak, S. Solujić, Int. J. Mol. Sci. 12, 2822–2841 (2011)

    Article  Google Scholar 

  7. J.-F. Cheng, A. Ishikawa, Y. Ono, T. Arrhenius, A. Nadzan, Bioorg. Med. Chem. Lett. 13, 3647–3650 (2003)

    Article  CAS  Google Scholar 

  8. S. Thareja, A. Verma, A. Kalra, S. Gosain, P.V. Rewatkar, G.R. Kokil, Acta Pol. Pharm. Res. 67, 423–427 (2010)

    CAS  Google Scholar 

  9. N. Jain, J. Xu, R.M. Kanojia, F. Du, G. Jian-Zhong, E. Pacia, M.-T. Lai, A. Musto, G. Allan, M. Reuman, J. Med. Chem. 52, 7544–7569 (2009)

    Article  CAS  Google Scholar 

  10. J. Mori, M. Iwashima, M. Takeuchi, H. Saito, Chem. Pharm. Bull. 54, 391–396 (2006)

    Article  CAS  Google Scholar 

  11. D.R. Anderson, S. Hegde, E. Reinhard, L. Gomez, W.F. Vernier, L. Lee, S. Liu, A. Sambandam, P.A. Snider, L. Masih, Bioorg. Med. Chem. Lett. 15, 1587–1590 (2005)

    Article  CAS  Google Scholar 

  12. C.K. Denish, K.P. Hetal, K.G. Nilesh, AJBPR 2, 126–130 (2012)

    Google Scholar 

  13. A. Maleki, RSC Adv. 4, 64169–64173 (2014)

    Article  CAS  Google Scholar 

  14. A. Maleki, M. Rabbani, Sh. Shahrokh, Appl. Organometal. Chem. 29, 809–814 (2015)

    Article  CAS  Google Scholar 

  15. A. Maleki, E. Akhlaghi, R. Paydar, Appl. Organometal. Chem. 30, 382–386 (2016)

    Article  CAS  Google Scholar 

  16. A. Maleki, M. Aghaei, N. Ghamari, Appl. Organometal. Chem. 30, 939–942 (2016)

    Article  CAS  Google Scholar 

  17. A. Maleki, M. Kamalzare, Catal. Commun. 53, 67–71 (2014)

    Article  CAS  Google Scholar 

  18. J.S. Lee, E.J. Lee, H.J. Hwang, Trans. Nonferrous Met. Soc. China 22, 702–706 (2012)

    Article  Google Scholar 

  19. C. Hui, C. Shen, J. Tian, L. Bao, H. Ding, C. Li, Y. Tian, X. Shi, H.-J. Gao, Nanoscale 3, 701–705 (2011)

    Article  CAS  Google Scholar 

  20. G. Fang, H. Chen, Y. Zhang, A. Chen, Int. J. Biol. Macromol. 88, 189–195 (2016)

    Article  CAS  Google Scholar 

  21. G. Yang, L. Zhang, Z. Liu, Z. Cheng, X. Zhu, J. Mater. Chem. B 3, 2786–2800 (2015)

    Article  Google Scholar 

  22. Q. Zhang, H. Su, J. Luo, Y. Wei, Green Chem. 14, 201–208 (2012)

    Article  CAS  Google Scholar 

  23. Q. Zhang, H. Su, J. Luo, Y. Wei, Catal. Sci. Technol. 3, 235–243 (2013)

    Article  Google Scholar 

  24. J. Safari, Z. Zarnegar, J. Mol. Struct. 1072, 53–60 (2014)

    Article  CAS  Google Scholar 

  25. A. Maleki, R. Rahimi, S. Maleki, Synth. Met. 194, 11–18 (2014)

    Article  Google Scholar 

  26. K. Pradhan, S. Paul, A.R. Das, Catal. Sci. Technol. 4, 822–831 (2014)

    Article  CAS  Google Scholar 

  27. S. Kazemi, A. Javanshir, Maleki, M. Safari, H.R. Khavasi, Tetrahedron Lett. 53, 6977–6981 (2012)

    Article  CAS  Google Scholar 

  28. A. Molla, S. Hussain, RSC Adv. 4, 29750–29758 (2014)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge the partial support from the Research Council of the Iran University of Science and Technology.

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Authors and Affiliations

  1. Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran

    Ali Maleki & Sepide Azadegan

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  1. Ali Maleki
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  2. Sepide Azadegan
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Correspondence to Ali Maleki.

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Maleki, A., Azadegan, S. Amine-Functionalized Silica-Supported Magnetic Nanoparticles: Preparation, Characterization and Catalytic Performance in the Chromene Synthesis. J Inorg Organomet Polym 27, 714–719 (2017). https://doi.org/10.1007/s10904-017-0514-z

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  • DOI: https://doi.org/10.1007/s10904-017-0514-z

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