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Nanomagnetically modified polyphosphoric acid (NiFe2O4@SiO2–PPA): an efficient, fast, and reusable catalyst for the synthesis of 2-thioxoquinazolinones under solvent-free conditions

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Abstract

Polyphosphoric acid functionalized silica-coated magnetic nanoparticles with core–shell structure (NiFe2O4@SiO2–PPA) has been used as a magnetically recyclable green catalyst for the one-pot three-component synthesis of 2-thioxoquinazolinones by the reaction of isatoic anhydride, primary amines and thiourea under neat conditions. The catalyst is readily recovered by simple magnetic decantation and can be recycled five times with no significant loss of catalytic activity.

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References

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

    Article  CAS  Google Scholar 

  2. M.M. Lin, H.H. Kim, H. Kim, M. Muhammed, D.K. Kim, Nano Rev. 1, 4883 (2010)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  4. A. Hu, G.T. Yee, W. Lin, J. Am. Chem. Soc. 127, 12486 (2005)

    Article  CAS  Google Scholar 

  5. M. Mojtahedi, M.S. Abaee, T. Alishiri, Tetrahedron Lett. 50, 2322 (2009)

    Article  CAS  Google Scholar 

  6. L. Mamani, A. Heydari, M. Sheykhan, Appl. Catal. A 384, 122 (2010)

    Article  CAS  Google Scholar 

  7. B. Karimi, E. Farhangi, Adv. Synth. Catal. 355, 508 (2013)

    CAS  Google Scholar 

  8. F. Shahbazi, K. Amani, Catal. Commun. 55, 57 (2014)

    Article  CAS  Google Scholar 

  9. S. Rostamnia, K. Lamei, M. Mohammadquli, M. Sheykhan, A. Heydari, Tetrahedron Lett. 53, 5257 (2012)

    Article  CAS  Google Scholar 

  10. L. Mamani, M. Sheykhan, A. Heydari, M. Faraji, Y. Yamini, Appl. Catal. A 377, 64 (2010)

    Article  CAS  Google Scholar 

  11. D.W. Hein, R.J. Alheim, J.J. Leavitt, J. Am. Chem. Soc. 79, 427 (1957)

    Article  CAS  Google Scholar 

  12. E. Alcalde, I. Dinarés, L. Pérez-García, T. Roca, Synthesis 1992, 395 (1992)

    Article  Google Scholar 

  13. V. Aagarsamy, R. Giridhar, M.R. Yadav, R. Revathi, K. Ruckmani, Ind. J. Pharm. Sci. 68, 532 (2006)

    Article  Google Scholar 

  14. A. Rajasekaran, V. Rajamanickam, S. Darlinquine, Eur. Rev. Med. Pharmacol. Sci. 17, 95 (2013)

    CAS  Google Scholar 

  15. R. Cortez, I.A. Rivero, R. Somanathan, G. Aguirre, F. Ramirez, E. Hong, Synth. Commun. 21, 285 (1991)

    Article  CAS  Google Scholar 

  16. V. Alagarsamy, R. Giridhar, M.R. Yadav, J. Pharm. Pharmacol. 58, 1249 (2006)

    Article  CAS  Google Scholar 

  17. M. Redondo, J.G. Zarruk, P. Ceballos, D.I. Perez, C. Perez, A.P. Castillo, M.A. Moro, J. Brea, C. Val, M.I. Cadavid, M.I. Loza, N.E. Campillo, A. Martinez, C. Gil, Eur. J. Med. Chem. 47, 175 (2012)

    Article  CAS  Google Scholar 

  18. H.M. Jen, H.L. Jiau, K.S. Chu, X.Y. Bastow, B. Kenneth, N.K. Hamel, E. Lee, K. Hsiung, J. Med. Chem. 43, 4479 (2000)

    Article  Google Scholar 

  19. S.K. Krishnan, S. Ganguly, R. Veerasamy, B. Jan, Eur. Rev. Med. Pharmacol. Sci. 15, 673 (2011)

    CAS  Google Scholar 

  20. F. Wanga, P. Zhaoa, C. Xi, Tetrahedron Lett. 52, 231 (2011)

    Article  Google Scholar 

  21. S. Allameh, M.M. Heravi, M.M. Hashemi, F.F. Bamoharram, Chin. Chem. Lett. 22, 131 (2011)

    Article  CAS  Google Scholar 

  22. A. Saeed, U. Shaheena, M. Bolteb, J. Chin. Chem. Soc. 57, 82 (2010)

    Article  CAS  Google Scholar 

  23. A. Khojastehnezhad, F. Moeinpour, A. Davoodnia, Chin. Chem. Lett. 22, 807 (2011)

    Article  CAS  Google Scholar 

  24. A. Khojastehnezhad, F. Moeinpour, A.R. Shams, Synth. React. Inorg. Met. Org. Chem. 42, 273 (2012)

    Article  CAS  Google Scholar 

  25. F. Moeinpour, N. Dorostkar-Ahmadi, A. Sardashti-Birjandi, A. Khojastehnezhad, M. Vafaei, Res. Chem. Intermed. 40, 3145 (2014)

    Article  CAS  Google Scholar 

  26. F. Moeinpour, N. Dorostkar, M. Vafaei, Synth. Commun. 42, 2367 (2012)

    Article  CAS  Google Scholar 

  27. A. Khojastehnezhad, M. Rahimizadeh, F. Moeinpour, H. Eshghi, M. Bakavoli, C. R. Chim. 17, 459 (2014)

    Article  CAS  Google Scholar 

  28. A. Khojastehnezhad, M. Rahimizadeh, H. Eshghi, F. Moeinpour, M. Bakavoli, Chin. J. Cat. 35, 376 (2014)

    Article  CAS  Google Scholar 

  29. H. Eshghi, A. Khojastehnezhad, S.M. Seyedi, F. Moeinpour, M. Abbasi, M. Bakavoli, RSC Adv. 4, 39782 (2014)

    Article  CAS  Google Scholar 

  30. M. Rahimizadeh, S.M. Seyedi, M. Abbasi, H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, J. Iranian, Chem. Soc. (2014). doi:10.1007/s13738-014-0546-z

    Google Scholar 

  31. D. Zins, V. Cabuil, R. Massart, J. Mol. Liq. 83, 217 (1999)

    Article  CAS  Google Scholar 

  32. R. Lakhan, M. Srivastava, Proc. Indian. Acad. Sci. Chem. Sci. 105, 11 (1993)

    CAS  Google Scholar 

  33. J. Azizian, A.A. Mohammadi, A.R. Karimi, Synth. Commun. 33, 415 (2003)

    Article  CAS  Google Scholar 

  34. D. Guo-lan, W. Man-Man, H. Zhi-Bin, S. Da-Qing, J. Het, Chem. 46, 645 (2009)

    Google Scholar 

  35. V.K. Tiwari, D.D. Singh, H.A. Hussain, B.B. Mishra, A. Singh, Monatsh. Chem. 139, 43 (2008)

    Article  CAS  Google Scholar 

  36. I. Yavari, S. Beheshti, Helv. Chim. Acta 94, 1825 (2011)

    Article  CAS  Google Scholar 

  37. T. Kappe, W. Steiger, E. Ziegler, Monatsh. Chem. 98, 214 (1967)

    Article  CAS  Google Scholar 

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Acknowledgment

The authors are grateful to Islamic Azad University, Bandar Abbas and Mashhad Branches for financial support.

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Correspondence to Farid Moeinpour.

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Eshghi, H., Khojastehnezhad, A., Moeinpour, F. et al. Nanomagnetically modified polyphosphoric acid (NiFe2O4@SiO2–PPA): an efficient, fast, and reusable catalyst for the synthesis of 2-thioxoquinazolinones under solvent-free conditions. Res Chem Intermed 41, 7915–7924 (2015). https://doi.org/10.1007/s11164-014-1866-4

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  • DOI: https://doi.org/10.1007/s11164-014-1866-4

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