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Using magnetic nanoparticles Fe3O4 as a reusable catalyst for the synthesis of pyran and pyridine derivatives via one-pot multicomponent reaction

Journal of the Iranian Chemical Society volume 12, pages 2075–2081 (2015)Cite this article

Abstract

An atom-economical, efficient and mild protocol is described for the synthesis of 2-amino-3-cyanopyridine and 2-amino-3-cyano-4H-pyran derivatives in the presence of high surface area Fe3O4 as a highly effective heterogeneous catalyst via one-pot multicomponent cyclo-condensation reaction.

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Scheme 1
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References

  1. P.L. Barili, G. Biagi, O. Livi, L. Mucciand, V.J. Scartoni, Heterocycl. Chem. 24, 997 (1987)

    CAS  Article  Google Scholar 

  2. M.T. Cocco, C. Congiu, V. Lilliu, V. Onnis, Eur. J. Med. Chem. 40, 1365 (2005)

    CAS  Article  Google Scholar 

  3. T.R. Reddy, R. Mutter, W. Heal, K. Guo, V.J. Gillet, S. Pratt, B. Chen, J. Med. Chem. 49, 607 (2006)

    CAS  Article  Google Scholar 

  4. G. Jones, A.R. Katritzky, C.W. Rees, E.F.V. Scriven, A. McKillop, Compr Heterocycl Chem II 5, 167 (1996)

    CAS  Google Scholar 

  5. J.P. Michael, Nat. Prod. Rep. 22, 627 (2005)

    CAS  Article  Google Scholar 

  6. X.S. Wang, D.Q. Shi, S.T. Tu, C.S. Yao, Synth. Commun. 33, 119 (2003)

    CAS  Article  Google Scholar 

  7. S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc., Chem. Commun. 17, 1202 (1988)

    Article  Google Scholar 

  8. C.J. Shishoo, M.B. Devani, V.S. Bhadti, S. Ananthan, G.V. Ullas, Tetrahedron Lett. 24, 4611 (1983)

    CAS  Article  Google Scholar 

  9. A.H. Adbel-Fattah, A.M. Hesien, S.A. Metwally, M.H. Elnagdi, Ann. Chem. 21, 585 (1989)

    Google Scholar 

  10. M. Mantri, O. De Graaf, J. Van Veldhoven, T. Mulder-Krieger, R. Link, H. De Vries, M.W. Beukers, J. Brussee, A.P. Ijzerman, J. Med. Chem. 51, 4449 (2008)

    CAS  Article  Google Scholar 

  11. 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)

    CAS  Article  Google Scholar 

  12. L.L. Andreani, E. Lapi, Bull. Chim. Farm. 99, 583 (1960)

    Google Scholar 

  13. R. Gupta, A. Jain, M. Jain, R. Joshi, Bull. Korean Chem. Soc. 31, 3180 (2010)

    CAS  Article  Google Scholar 

  14. F. Zhang, Y. Zhao, L. Sun, L. Ding, Y. Gu, P. Gong, Eur. J. Med. Chem. 46, 3149 (2011)

    CAS  Article  Google Scholar 

  15. D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 47, 63 (2010)

    CAS  Google Scholar 

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

    CAS  Article  Google Scholar 

  17. M.M. Heravi, B.A. Jani, F. Derikvand, F.F. Bamoharram, H.A. Oskooie, Catal. Commun. 10, 272 (2008)

    CAS  Article  Google Scholar 

  18. M.M. Heravi, Kh Bakhtiari, A. Fatehi, F. Bamoharram, Catal. Commun. 9, 289 (2008)

    CAS  Article  Google Scholar 

  19. M.M. Heravi, S. Sadjadi, J. Iran. Chem. Soc. 6, 1 (2009)

    CAS  Article  Google Scholar 

  20. T. Cheng, D. Zhang, H. Li, G. Liu, Green Chem. 16, 3401 (2014)

    CAS  Article  Google Scholar 

  21. R. Mr´owczy´nski, A. Nanb, J. Liebscher, RSC Adv. 4, 5927 (2014)

    Article  Google Scholar 

  22. M.M. Heravi, F. Mousavizadeh, N. Ghobadi, M. Tajbakhsh, Tetrahedron Lett. 55, 1226 (2014)

    CAS  Article  Google Scholar 

  23. H.A. Oskoole, M.M. Heravi, Kh Bakhtiari, V. Zadsirjan, F. Bamoharram, Synlett 11, 1768 (2007)

    Google Scholar 

  24. J.Y. Lek, L. Xi, B.E. Kardynal, L.H. Wong, Y.M. Lam, ACS Appl. Mater. 3, 287 (2011)

    CAS  Article  Google Scholar 

  25. M.M. Heravi, S. Moghimi, Curr. Org. Chem. 17, 504 (2013)

    Article  Google Scholar 

  26. F. Iskandar, Adv. Powder Technol. 20, 283 (2009)

    CAS  Article  Google Scholar 

  27. V.K. Sharma, R.A. Yngard, Y. Lin, Adv. Colloid Interface Sci. 145, 83 (2009)

    CAS  Article  Google Scholar 

  28. G.J. Hutchings, Catal. Today 100, 55 (2005)

    CAS  Article  Google Scholar 

  29. M.M. Heravi, E. Hashemi, S.Y. Shirazibeheshtiha, Kh Kamjou, M. Toolabi, N. Hosseintash, J. Mol. Catal. A: Chem. 392, 173 (2014)

    CAS  Article  Google Scholar 

  30. F. Bamoharram, M.M. Heravi, M. Roshani, J. Mol. Catal. A: Chem. 271, 126 (2007)

    CAS  Article  Google Scholar 

  31. M.M. Heravi, Gh Rajabzadeh, F. Bamoharram, J. Mol. Catal. A: Chem. 256, 238 (2006)

    CAS  Article  Google Scholar 

  32. E. Hashemi, S.Y. Shirazi Beheshtiha, S. Ahmadi, M.M. Heravi, Transit. Met. Chem. 39, 593 (2014)

    CAS  Article  Google Scholar 

  33. W.S. Chiu, S. Radiman, M.H. Abdullah, P.S. Khiew, N.M. Huang, R. Abd-Shukor, Mater. Chem. Phys. 106, 231 (2007)

    CAS  Article  Google Scholar 

  34. M.M. Heravi, M. Tajbakhsh, A.N. Ahmadi, B. Mohajerani, Monatsh. Chem. 137, 175 (2006)

    CAS  Article  Google Scholar 

  35. M.M. Heravi, Kh Bakhtiari, Z. Daroogheha, F. Bamoharram, Catal. Commun. 8, 1991 (2007)

    CAS  Article  Google Scholar 

  36. M.M. Heravi, M. Khorasani, F. Derikvand, H.A. Oskoole, F. Bamoharram, Catal. Commun. 8, 1886 (2007)

    CAS  Article  Google Scholar 

  37. M.M. Heravi, V. Zadsirjan, Kh Bakhtiari, Catal. Commun. 8, 315 (2007)

    CAS  Article  Google Scholar 

  38. M.M. Heravi, Kh Bakhtiari, V. Zadsirjan, Bioorg. Med. Chem. Lett. 17, 4262 (2007)

    CAS  Article  Google Scholar 

  39. M.M. Heravi, Kh Bakhtiari, Z. Daroogheha, F. Bamoharram, J. Mol. Catal. A: Chem. 273, 99 (2007)

    CAS  Article  Google Scholar 

  40. D. Astruc, F. Lu, J.R. Aranzaes, Angew. Chem. Int. Ed. 44, 7852 (2005)

    CAS  Article  Google Scholar 

  41. M.M. Heravi, T. Alishiri, Heterocycles 85, 545 (2012)

    CAS  Article  Google Scholar 

  42. G. Evanom, N. Blanchard, M. Toumi, Chem. Rev. 108, 3054 (2008)

    Article  Google Scholar 

  43. M.M. Heravi, Sh Asadi, B.M. Lashkariani, Mol. Divers. 17, 389 (2013)

    CAS  Article  Google Scholar 

  44. M.M. Heravi, F.K. Behbahani, M. Darai, H.A. Oskooie, Mol. Divers. 13, 375 (2009)

    CAS  Article  Google Scholar 

  45. M.M. Heravi, S. Moghimi, J. Iran. Chem. Soc. 8, 306 (2011)

    CAS  Article  Google Scholar 

  46. M. Negwar, Organic-chemical Drugs and Their Synonyms (Akademie, Berlin, 1994)

    Google Scholar 

  47. M.G. Dekamin, Z. Mokhtari, Z. Karimi, Sci. Iran. Trans. 18, 1356 (2011)

    CAS  Article  Google Scholar 

  48. M.M. Heravi, Z. Faghihi, J. Iran. Chem. Soc. 11, 209 (2014)

    CAS  Article  Google Scholar 

  49. F. Nemati, M.M. Heravi, R. Saeedi Rad, Chin. J. Catal. 33, 1825 (2012)

    CAS  Article  Google Scholar 

  50. F. Janati, M.M. Heravi, A.M. Shokraie, Synth. React. Org. Chem. 45, 1 (2015)

    CAS  Article  Google Scholar 

  51. T. Alishiri, H.A. Oskooei, M.M. Heravi, Synth. Commun. 43, 3357 (2013)

    CAS  Article  Google Scholar 

  52. S. Bakhshayesh, H. Dehghani, J. Iran. Chem. Soc. 11, 769 (2014)

    CAS  Article  Google Scholar 

  53. R. Rahimi, H. Kerdari, M. Rabbani, M. Shafiee, Desalination 280, 412 (2011)

    CAS  Article  Google Scholar 

  54. R. Rahimi, A. Tadjarodi, M. Rabbani, H. Kerdari, J. Supercond. Nov. Magn. 26, 219 (2013)

    CAS  Article  Google Scholar 

  55. J.B. Mamani, A.J. Costa-Filho, D.R. Cornejo, E.D. Vieira, L.F. Gamarra, Mater. Charact. 81, 28 (2013)

    CAS  Article  Google Scholar 

  56. M.G. Assy, S.H.A. Youssif, N.H. Ouf, Pol. J. Chem. 6, 896 (1995)

    Google Scholar 

  57. L. Zhi, C.M. Tegley, B. Pio, J.P. Edward, M. Motamedi, T.D. Jones, K.B. Marschke, D.E. Mais, B. Risek, W.T. Schrader, J. Med. Chem. 46, 4104 (2003)

    CAS  Article  Google Scholar 

  58. S. Khaksar, M. Yaghoobi, J. Fluor. Chem. 142, 41 (2012)

    CAS  Article  Google Scholar 

  59. Y.S. Beheshtia, M. Khorshidi, M.M. Heravi, B. Baghernejad, Eur. J. Chem. 3, 232 (2010)

    Article  Google Scholar 

  60. J. Tang, L. Wang, Y. Yao, L. Zhang, W. Wanga, Tetrahedron Lett. 52, 509 (2011)

    CAS  Article  Google Scholar 

  61. G.M. Nazeruddin, Y.I. Shaikh, A.A. Shaikh, RJPBCS 5, 1773 (2014)

    Google Scholar 

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Acknowledgments

M. M. H is thankful to Iran National Science Foundation (INSF) for partial financial assistance allocated for project 93043105.

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Authors and Affiliations

  1. Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran

    Majid M. Heravi, S. Yahya Shirazi Beheshtiha, Mahzad Dehghani & Nastaran Hosseintash

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  1. Majid M. Heravi
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  2. S. Yahya Shirazi Beheshtiha
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  3. Mahzad Dehghani
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  4. Nastaran Hosseintash
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Correspondence to Majid M. Heravi.

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Heravi, M.M., Yahya Shirazi Beheshtiha, S., Dehghani, M. et al. Using magnetic nanoparticles Fe3O4 as a reusable catalyst for the synthesis of pyran and pyridine derivatives via one-pot multicomponent reaction. J IRAN CHEM SOC 12, 2075–2081 (2015). https://doi.org/10.1007/s13738-015-0684-y

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  • DOI: https://doi.org/10.1007/s13738-015-0684-y

Keywords

  • Pyran
  • Pyridine
  • Magnetic nanoparticles Fe3O4
  • Multicomponent reaction
  • Recyclable catalyst
  • Green chemistry