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H3PMo12O40 immobilized chitosan/Fe3O4 as a novel efficient, green and recyclable nanocatalyst in the synthesis of pyrano-pyrazole derivatives

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Abstract

A novel nanomagnetic composite heteropolyacid immobilized chitosan/Fe3O4 was prepared via a facile one-pot synthetic approach. This magnetically recoverable nanocatalyst, H3PMo12O40/chitosan/Fe3O4 (PMo/chit/Fe3O4), was fully characterized by XRD, FTIR, SEM and EDX analysis methods. A rapid, efficient and the chemoselective synthesis of different pyrano-pyrazole derivatives was achieved in excellent yields via a one-pot four-component reaction in the presence of catalytic amount of PMo/Chit/Fe3O4.

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References

  1. I.V. Kozhevnikov, Catalysis by Polyoxometalates (Wiley, Chichester, 2002)

    Google Scholar 

  2. I.V. Kozhevnikov, J. Mol. Catal. A Chem. 305, 104 (2009)

    Article  CAS  Google Scholar 

  3. P. Sharma, A. Patel, Appl. Surf. Sci. 255, 7635 (2009)

    Article  CAS  Google Scholar 

  4. L.T.A. Sofia, A. Krishnan, M. Sankar, N.K.K. Raj, P. Manikandan, P.R. Rajamohanan, T.G. Ajithkumar, J. Phys. Chem. C 113, 21114 (2009)

    Article  CAS  Google Scholar 

  5. F.F. Bamoharram, A. Ahmadpour, M.M. Heravi, NANO 6, 349 (2011)

    Article  CAS  Google Scholar 

  6. P. Sharma, S. Vyas, A. Patel, J. Mol. Catal. A 214, 281 (2004)

    Article  CAS  Google Scholar 

  7. R. Mrowczyński, A. Nanb, J. Liebscher, RSC Adv. 4, 5927 (2014)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. B. Tanhaei, A. Ayati, M. Lahtinen, M. Sillanpää, Chem. Eng. J. 259, 1 (2015)

    Article  CAS  Google Scholar 

  12. D.J. Kim, M.J. Jo, S.Y. Nam, J. Ind. Eng. Chem. 21, 36 (2015)

    Article  CAS  Google Scholar 

  13. D.H.K. Reddy, S.M. Lee, Adv. Colloid Interface Sci. 201–202, 68 (2013)

    Article  Google Scholar 

  14. A. Naghipour, A. Fakhri, Catal. Commun. 73, 39 (2016)

    Article  CAS  Google Scholar 

  15. J. Safari, L. Javadian, Ultrason. Sonochem. 22, 341 (2015)

    Article  CAS  Google Scholar 

  16. A. Kong, P. Wang, H. Zhanga, F. Yang, S.P. Huang, Y. Shana, App. Catal. A Gen. 417–418, 183 (2012)

    Article  Google Scholar 

  17. E. Saxon, J.I. Armstrong, C.R. Bertozzi, Org. Lett. 2, 2141 (2000)

    Article  CAS  Google Scholar 

  18. L.A. Shastri, M.V. Kulkarni, V. Gupta, N. Sharma, Synth. Commun. 38, 1407 (2008)

    Article  CAS  Google Scholar 

  19. D.J. Ramon, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)

    Article  CAS  Google Scholar 

  20. L. Weber, Curr. Med. Chem. 9, 2085 (2002)

    Article  CAS  Google Scholar 

  21. J. Zhu, H. Bienaymé, Multicomponent Reactions (Wiley-VCH, Weinheim, 2005)

    Book  Google Scholar 

  22. A. Dömling, Chem. Rev. 106, 17 (2006)

    Article  Google Scholar 

  23. C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004(24), 4957 (2004)

    Article  Google Scholar 

  24. R.V.A. Orru, M. de Greef, Synthesis 2003(10), 1471 (2003)

  25. H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 6, 3321 (2000)

    Article  Google Scholar 

  26. A. Ulaczyk-Lesanko, D.G. Hall, Curr. Opin. Chem. Biol. 9, 266 (2005)

    Article  CAS  Google Scholar 

  27. T. Ueda, H. Mase, N. Oda, I. Ito, Chem. Pharm. Bull. 29, 3522 (1981)

    Article  CAS  Google Scholar 

  28. S.C. Kuo, L.J. Huang, H. Nakamura, J. Med. Chem. 27, 539 (1984)

    Article  CAS  Google Scholar 

  29. H. Stegelmeier, W. Brandes, US4515801 (1985)

  30. G. Feuer, Progress in Medicinal Chemistry (North-Holland, New York, 1974)

    Google Scholar 

  31. A.A. Deana, G.E. Stokker, E.M. Schultz, R.L. Smith, E.J. Cragoe Jr., H.F. Russo, L.S. Watson, J. Med. Chem. 26, 580 (1983)

    Article  CAS  Google Scholar 

  32. M.M. Heravi, T. Alishiri, Adv. Heterocycl. Chem. 113, 1 (2014)

    Article  CAS  Google Scholar 

  33. M.M. Heravi, B. Talaei, Adv. Heterocycl. Chem. 113, 143 (2014)

    Article  CAS  Google Scholar 

  34. M.M. Heravi, S. Khaghaninejad, M. Mostofi, Adv. Heterocycl. Chem. 112, 1 (2014)

    Article  CAS  Google Scholar 

  35. M.M. Heravi, S. Khaghaninejad, N. Nazari, Adv. Heterocycl. Chem. 112, 183 (2014)

    Article  CAS  Google Scholar 

  36. M.M. Heravi, B. Talaei, Adv. Heterocycl. Chem. 114, 147 (2015)

    Article  CAS  Google Scholar 

  37. M.M. Heravi, V.F. Vavsari, Adv. Heterocycl. Chem. 114, 77 (2015)

    Article  CAS  Google Scholar 

  38. S. Khaghaninejad, M.M. Heravi, Adv. Heterocycl. Chem. 111, 95 (2014)

    Article  CAS  Google Scholar 

  39. M.M. Heravi, V. Zadsirjan, Adv. Heterocycl. Chem. 117, 261 (2015)

    Article  Google Scholar 

  40. M.M. Heravi, M. Vazin Fard, Z. Faghihi, Green Chem. Lett. 6, 282 (2013)

    Article  CAS  Google Scholar 

  41. M.M. Heravi, S. Sadjadi, H. Oskoole, Catal. Commun. 9, 470 (2008)

    Article  CAS  Google Scholar 

  42. F.F. Bamoharram, M.M. Heravi, M. Roshani, J. Mol. Catal. A Chem 267, 241 (2007)

    Article  CAS  Google Scholar 

  43. F.F. Bamoharram, A. Ahmadpour, M.M. Heravi, A. Ayati, H. Rashidi, B. Tanhaei, Synth. React. Inorg. Met. Org. Chem. 42, 209 (2012)

    Article  CAS  Google Scholar 

  44. A. Ayati, A. Ahmadpour, F.F. Bamoharram, M.M. Heravi, M. Salanpaa, Gol Bull. 45, 145 (2012)

    Article  CAS  Google Scholar 

  45. A. Ayati, A. Ahmadpour, F.F. Bamoharram, B. Tanhaei, M. Mänttäri, M. Lahtinen, M. Sillanpää, Sep. Pur. Technol. 133, 415 (2014)

    Article  CAS  Google Scholar 

  46. F.F. Bamoharram, M. Poorzaki, A. Morsali, S. Beiramabadi, A. Ahmadpour, M.M. Heravi, A. Ayati, Micro Nano Lett. 9, 482 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. M.R. Nabid, R. Sedghi, S. Gholami, H.A. Oskooie, M.M. Heravi, Photochem. Photobiol. 89, 24 (2013)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  50. M.M. Heravi, Y.S. Beheshtiha, M. Dehghani, N. Hosseintash, J. Iran. Chem. Soc. 12, 2075 (2015)

    Article  CAS  Google Scholar 

  51. F. Nemati, M.M. Heravi, A. Elhampour, RSC Adv. 5, 45775 (2015)

    Article  CAS  Google Scholar 

  52. B. Tanhaei, A. Ayati, F.F. Bamoharram, M. Lahtinenc, M. Sillanpää, J. Chem. Technol. Biotechnol. 91, 1452 (2016)

    Article  CAS  Google Scholar 

  53. R. Mirsafaei, M.M. Heravi, S. Ahmadi, M.H. Moslemin, T. Hosseinnejad, J. Mol. Catal. A Chem. 402, 100 (2015)

    Article  CAS  Google Scholar 

  54. M.M. Heravi, M. Saeedi, Y.S. Beheshtiha, H.A. Oskooie, Heterocycles 83, 535 (2011)

    Article  CAS  Google Scholar 

  55. S. Wang, R. Tang, Y. Zhang, T. Chen, G. Wang, Chem. Eng. Sci. 138, 93 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

M.M.H. is thankful to Iran National Science Foundation (INSF) and Alzahra University for the partial financial support.

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Authors and Affiliations

  1. Department of Chemical Engineering, Quchan University of Advanced Technology, Quchan, Iran

    Ali Ayati & Bahareh Tanhaei

  2. Laboratory of Green Chemistry, LUT Chemtech, Lappeenranta University of Technology, Sammonkatu 12, 50130, Mikkeli, Finland

    Ali Ayati & Mika Sillanpaa

  3. Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

    Majid M. Heravi & Mansoureh Daraie

  4. Department of Chemistry, Mashhad Branch-Islamic Azad University, Mashhad, Iran

    Fatemeh F. Bamoharram

  5. Department of Civil and Environmental Engineering, Florida International University, Miami, FL, 33174, USA

    Mika Sillanpaa

Authors
  1. Ali Ayati
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  2. Majid M. Heravi
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  4. Bahareh Tanhaei
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Correspondence to Majid M. Heravi.

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Ayati, A., Heravi, M.M., Daraie, M. et al. H3PMo12O40 immobilized chitosan/Fe3O4 as a novel efficient, green and recyclable nanocatalyst in the synthesis of pyrano-pyrazole derivatives. J IRAN CHEM SOC 13, 2301–2308 (2016). https://doi.org/10.1007/s13738-016-0949-0

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  • DOI: https://doi.org/10.1007/s13738-016-0949-0

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