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Synthesis and characterization of pyridine-4-carboxylic acid functionalized Fe3O4 nanoparticles as a magnetic catalyst for synthesis of pyrano[3,2-b]pyranone derivatives under solvent-free conditions

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Abstract

Pyridine-4-carboxylic acid (PYCA) functionalized Fe3O4 nanoparticles as an organic–inorganic hybrid heterogeneous catalyst was fabricated and characterized by FT-IR, XRD, TGA, TEM, SEM, and VSM techniques. The catalytic activity of the magnetic catalyst was probed through one-pot synthesis of pyrano[3,2-b]pyranone derivatives from three component reactions of aromatic aldehydes, kojic acid, and ethyl cyanoacetate under solvent-free conditions. Some advantages of this protocol are its environmentally benign method, simple procedure, high yields, and short reaction time. The catalyst was readily separated using an external magnet and reusable without significant loss of its catalytic efficiency.

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References

  1. A. Tiwari, A.K. Mishra, H. Kobayashi, A.P.F. Turner, Intelligent Nanomaterials: Processes, Properties, and Applications (John Wiley & Sons, Inc., New Jersey, 2012)

    Book  Google Scholar 

  2. B. Hu, J. Pan, H.L. Yu, J.W. Liu, J.H. Xu, Process Biochem. 44, 1019–1024 (2009)

    Article  CAS  Google Scholar 

  3. K.J. Klabunde, R. Mulukutla, Chemical and Catalytic Aspects of Nanocrystals. Nanoscale Materials in Chemistry (Wiley Interscience, NewYork, 2001)

    Book  Google Scholar 

  4. C.N.R. Rao, A. Müller, K. Anthony, Nanomaterials Chemistry: Recent Developments and New Directions (John Wiley & Sons, Inc., New Jersey, 2007)

    Book  Google Scholar 

  5. A.H. Lu, E.L. Salabas, F. Schuth, Angew. Chem. Int. Ed. 46, 1222–1244 (2007)

    Article  CAS  Google Scholar 

  6. C.S. Gill, B.A. Price, C.W. Jones, J. Catal. 251, 145–152 (2007)

    Article  CAS  Google Scholar 

  7. A. Taher, J.B. Kim, J.Y. Jung, W.S. Ahn, M.J. Jin, Synlett 15, 2477–2482 (2009)

    Google Scholar 

  8. O.C. Dalaigh, A.S. Corr, Y. Gunko, J.S. Connon, Angew. Chem. Int. Ed. 46, 4329–4332 (2007)

    Article  CAS  Google Scholar 

  9. Y. Zhang, Y. Zhao, C. Xia, J. Mol. Catal. A: Chem. 306, 107–112 (2009)

    Article  CAS  Google Scholar 

  10. D. Wang, D. Astruc, Chem. Rev. 114, 6949–6985 (2014)

    Article  CAS  Google Scholar 

  11. Q.M. Kainz, O. Reiser, Acc. Chem. Res. 47, 667–677 (2014)

    Article  CAS  Google Scholar 

  12. R.B. Nasir Baig, M.N. Nadagouda, R.S. Varma, Coord. Chem. Rev. 287, 137–156 (2014)

    Article  Google Scholar 

  13. J. Zhu, H. Bienayme, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  14. A. Dömling, Chem. Rev. 106, 17–89 (2006)

    Article  Google Scholar 

  15. S. Jimenez-Alonso, H. Chavez, A. Estevez-Braan, A. Ravelo, G. Feresin, A. Tapia, Tetrahedron 64, 8938–8942 (2008)

    Article  CAS  Google Scholar 

  16. D.F. Tejedor, G. Tellado, Chem. Soc. Rev. 36, 484–491 (2007)

    Article  CAS  Google Scholar 

  17. A. Nefzi, J.M. Ostresh, R.A. Houghten, Chem. Rev. 97, 449–472 (1997)

    Article  CAS  Google Scholar 

  18. L.A. Thompson, Curr. Opin. Chem. Biol. 4, 324–337 (2000)

    Article  CAS  Google Scholar 

  19. A. Dömling, Curr. Opin. Chem. Biol. 6, 306–313 (2002)

    Article  Google Scholar 

  20. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517–520 (1993)

    Article  CAS  Google Scholar 

  21. F.M. Uckun, C. Mao, A.O. Vassilev, H. Huang, S.T. Jan, Bioorg. Med. Chem. Lett. 10, 541–545 (2000)

    Article  CAS  Google Scholar 

  22. R. Gonzalez, N. Martin, C. Seoane, J.L. Marco, A. Albert, F.H. Cano, Tetrahedron Lett. 33, 3809–3812 (1992)

    CAS  Google Scholar 

  23. D. Armesto, W.M. Horspool, N. Martin, A. Ramos, C. Seaone, J. Org. Chem. 54, 3069–3072 (1989)

    Article  CAS  Google Scholar 

  24. S. Asghari, M. Ahmadipour, Acta. Chem. Slov. 57, 953–956 (2010)

    CAS  Google Scholar 

  25. M.B. Miya, Y.J. Prakash Raob, G.L.D. Krupadanam, Heterocycl. Lett. 2, 214–217 (2012)

    Google Scholar 

  26. S. Paul, P. Bhattacharyya, A.R. Das, Tetrahedron Lett. 52, 4636–4641 (2011)

    Article  CAS  Google Scholar 

  27. L.M. Wang, N. Jiao, J. Qiu, J.J. Yu, J.Q. Liu, F.L. Guo, Y. Liu, Tetrahedron 66, 339–343 (2010)

    Article  CAS  Google Scholar 

  28. H.J. Wang, J. Lu, Z.H. Zhang, Monatsh. Chem. 141, 1107–1112 (2010)

    Article  CAS  Google Scholar 

  29. M. Saeedi, M.M. Heravi, Y.S. Beheshtiha, H.A. Oskooie, Tetrahedron 66, 5345–5348 (2010)

    Article  CAS  Google Scholar 

  30. U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Tetrahedron Lett. 52, 5817–5819 (2011)

    Article  CAS  Google Scholar 

  31. A. Samadi, D. Silva, M. Chioua, L. Infantes, E. Soriano, J. Marco-Contelles, Mol. Divers. 19, 103–122 (2015)

    Article  CAS  Google Scholar 

  32. Y. Peng, G. Song, Catal. Commun. 8, 111–114 (2007)

    Article  CAS  Google Scholar 

  33. S. Asghari, R. Baharfar, M. Alimi, M. Ahmadipour, M. Mohseni, Monatsh. Chem. 145, 1337–1342 (2014)

    Article  CAS  Google Scholar 

  34. T. Wejrzanowski, R. Pielaszek, A. Opalińska, H. Matysiak, W. Lojkowski, K.J. Kurzydlowski, Appl. Surf. Sci. 253, 204–208 (2006)

    Article  CAS  Google Scholar 

  35. R. Pielaszek, J. Appl. Crystallogr. 1, 43–50 (2003)

    Google Scholar 

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Acknowledgments

This research was supported by the Research Council of the University of Mazandaran in Iran.

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Correspondence to Sakineh Asghari.

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Asghari, S., Mohammadnia, M. Synthesis and characterization of pyridine-4-carboxylic acid functionalized Fe3O4 nanoparticles as a magnetic catalyst for synthesis of pyrano[3,2-b]pyranone derivatives under solvent-free conditions. Res Chem Intermed 42, 1899–1911 (2016). https://doi.org/10.1007/s11164-015-2124-0

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  • DOI: https://doi.org/10.1007/s11164-015-2124-0

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