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Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives

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Abstract

Magnetically separable Fe3O4 nanoparticles were used as an environmental friendly catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono- and bis-1,4-dihydropyridine derivatives via three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively. These reactions were carried out in EtOH and at reflux. Fe3O4 nanoparticles can be magnetically separated from the reaction mixture by a magnet and recycled without significant loss of catalytic activity.

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References

  1. J. Zhu, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  2. L.F. Tietze, Chem. Rev. 96, 115 (1996)

    Article  CAS  Google Scholar 

  3. L.F. Tietze, U. Beifuss, Angew. Chem. 105, 137 (1993)

    Article  CAS  Google Scholar 

  4. D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 103, 893 (2003)

    Article  CAS  Google Scholar 

  5. A.S. Al-bogami, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1171-7

    Google Scholar 

  6. R. Sandaroos, S. Damavandi, Res. Chem. Intermed. 39, 4167 (2013)

    Article  CAS  Google Scholar 

  7. R.M. Shaker, Arkivoc ix, 59 (2006)

    Google Scholar 

  8. F. Bellina, R. Rossi, Tetrahedron 62, 7213 (2006)

    Article  CAS  Google Scholar 

  9. M. Abaszadeh, M. Seifi, Org. Biomol. Chem. 12, 7859 (2014)

    Article  CAS  Google Scholar 

  10. P.D. Mehta, N.P.S. Sengar, A.K. Pathak, Eur. J. Med. Chem. 45, 5541 (2010)

    Article  CAS  Google Scholar 

  11. A.R. Bhat, F. Athar, A. Azam, Eur. J. Med. Chem. 44, 426 (2009)

    Article  CAS  Google Scholar 

  12. P.F. Iqbal, H. Parveen, A.R. Bhat, F. Hayat, A. Azam, Eur. J. Med. Chem. 44, 4747 (2009)

    Article  CAS  Google Scholar 

  13. S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35, 3750 (1975)

    CAS  Google Scholar 

  14. J. Davoll, J. Clarke, E.F. Eislager, J. Med. Chem. 15, 837 (1972)

    Article  CAS  Google Scholar 

  15. T.N. Shwetaa, S. Gupta, Bioorg. Med. Chem. Lett. 14, 3913 (2004)

    Article  Google Scholar 

  16. A.M. El-Agrody, M.H. El-Hakium, M.S. Abd El-Latif, A.H. Fekry, E.S.M. El-Sayed, K.A. El-Gareab, Acta Pharm. 50, 111 (2000)

    CAS  Google Scholar 

  17. V.K. Ahluwalia, R. Batla, A. Khurana, R. Kumar, Indian J. Chem. Sec. B. 29, 1141 (1990)

    Google Scholar 

  18. J.L. Wang, D. Liu, Z.J. Zhang, S. Shan, X. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z. Huang, Proc. Natl. Acad. Sci. U.S.A. 97, 7124 (2000)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  20. M. Kidwai, S. Saxena, M.K.R. Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295 (2005)

    Article  CAS  Google Scholar 

  21. D. Heber, C. Heers, U. Ravens, Pharmazie 48, 537 (1993)

    CAS  Google Scholar 

  22. D.M. Stout, A. Meyers, Chem. Rev. 82, 223 (1982)

    Article  CAS  Google Scholar 

  23. R. Boer, V. Gekeler, Drugs Fut. 20, 499 (1995)

    Google Scholar 

  24. M. Ramesh, W.V. Matowe, J. Med. Chem. 41, 509 (1998)

    Article  CAS  Google Scholar 

  25. S.R. Pattan, A.N. Parate, Indian. J. Heterocycl. Chem. 12, 387 (2003)

    CAS  Google Scholar 

  26. Y.S. Sadanandam, M.M. Shetty, Eur. J. Med. Chem. 29, 975 (1994)

    Article  CAS  Google Scholar 

  27. K. Cooper, M.J. Fray, J. Med. Chem. 35, 3115 (1992)

    Article  CAS  Google Scholar 

  28. S.R. Agudoawu, E.E. Knaus, J. Heterocycl. Chem. 37, 303 (2000)

    Article  CAS  Google Scholar 

  29. A. Shafiee, N. Rastakari, Daru 12, 81 (2004)

    CAS  Google Scholar 

  30. M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron 69, 1074 (2013)

    Article  CAS  Google Scholar 

  31. H.R. Safaei, M. Shekouhy, A. Shirinfeshan, S. Rahmanpur, Mol. Divers. 16, 669 (2012)

    Article  CAS  Google Scholar 

  32. M. Seifi, H. Sheibani, Catal. Lett. 126, 275 (2008)

    Article  CAS  Google Scholar 

  33. T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, X.R. Song, Synlett, 2001 (2003)

  34. C. Lu, X.J. Huang, Y.Q. Li, M.Y. Zhou, W. Zheng, Monatsh. Chem. 140, 45 (2009)

    Article  Google Scholar 

  35. S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)

    Article  CAS  Google Scholar 

  36. M.R. Naimi-jamal, S. Mashkouri, A. Sharifi, Mol. Divers. 14, 473 (2010)

    Article  CAS  Google Scholar 

  37. M.M. Heravi, B. Baghernejad, H.A. Oskooie, J. Chin. Chem. Soc. 55, 659 (2008)

    Article  CAS  Google Scholar 

  38. M. Abaszadeh, M. Seifi, Lett. Org. Chem. 12, 271 (2015)

    Article  CAS  Google Scholar 

  39. F. You-Jiana, M. Chun-Baoa, G. Yuanb, T. Shu-Jiang, F. Fang, S. Da-Qing, Chin. J. Chem. 22, 622 (2004)

    Google Scholar 

  40. B.V. Lichitsky, A.A. Dudinov, M.M. Krayushkin, Arkivoc ix, 73 (2001)

    Google Scholar 

  41. M. Abaszadeh, M. Seifi, A. Asadipour, Res. Chem. Intermed. 41, 5129 (2014)

    Google Scholar 

  42. S. Sa, M.B. Gawande, A. Velhinho, J.P. Veiga, N. Bundaleski, J. Trigueiro, A. Tolstogouzov, O.M.N.D. Teodoro, R. Zboril, R.S. Varma, P.S. Branco, Green Chem. 16, 3494 (2014)

    Article  CAS  Google Scholar 

  43. M.B. Gawande, A.K. Rathi, I.D. Nogueira, R.S. Varma, P.S. Branco, Green Chem. 15, 1895 (2013)

    Article  CAS  Google Scholar 

  44. D. Wang, D. Astruc, Chem. Rev. 114, 6949 (2014)

    Article  CAS  Google Scholar 

  45. M.B. Gawande, R. Luque, R. Zboril, Chem. Cat. Chem. 6, 3312 (2014)

    CAS  Google Scholar 

  46. M.B. Gawande, Y. Monga, R. Zboril, R.K. Sharma, Coord. Chem. Rev. 288, 118 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. M.A. Ghasemzadeh, J. Safaei-Ghomi, S. Zahedi, J. Serb. Chem. Soc. 78, 769 (2013)

    Article  CAS  Google Scholar 

  49. B. Zeynizadeh, M. Karimkoshteh, J. Nanostruct. Chem. 3, 57 (2013)

    Article  Google Scholar 

  50. H.Y. Lü, S.H. Yang, J. Deng, Z.H. Zhang, Aust. J. Chem. 63, 1290 (2010)

    Article  Google Scholar 

  51. M. Nikpassand, L. Zare, T. Shafaati, S. Shariati, Chin. J. Chem. 30, 604 (2012)

    Article  CAS  Google Scholar 

  52. M.A. Ghasemzadeh, J. Safaei-Ghomi, H. Molaei, C. R. Chim. 15, 969 (2012)

    Article  CAS  Google Scholar 

  53. T. Zeng, W.W. Chen, C.M. Cirtiu, A. Moores, G. Song, C.J. Li, Green Chem. 12, 570 (2010)

    Article  CAS  Google Scholar 

  54. Z. Karimi-Jaberi, Z. Takmilifard, Eur. Chem. Bull. 2, 211 (2013)

    CAS  Google Scholar 

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Acknowledgments

The authors express their great appreciation to the Pharmaceutics Research Center, Institute of Neuropharmacology, Kerman University of Medical Sciences, for supporting this investigation.

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Correspondence to Mehdi Abaszadeh.

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Amirheidari, B., Seifi, M. & Abaszadeh, M. Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives. Res Chem Intermed 42, 3413–3423 (2016). https://doi.org/10.1007/s11164-015-2220-1

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