Heteropolyacid supported on amine-functionalized halloysite nano clay as an efficient catalyst for the synthesis of pyrazolopyranopyrimidines via four-component domino reaction

Abstract

An efficient heterogeneous hybrid catalyst was developed by functionalization of halloysite clay nanotubes by γ-aminopropyltriethoxysilane and then immobilization of a Keggin type heteropolyacid, phosphotungstic acid. This hybrid catalyst was characterized by SEM/EDX, FTIR and XRD and its catalytic activity for the synthesis of pyrazolopyranopyrimidine derivatives via four-component domino reaction of barbituric acid, hydrazine hydrate, ethyl acetoacetate and benzaldehyde was investigated. The results indicated that the hybrid system can promote the reaction to afford the desired products in high yields and short reaction times. The superior catalytic activity of this system was confirmed when compared with those reported, previously. Moreover, this novel heterogeneous catalyst was found to be easily separable and recyclable. It was re-used at least three times with negligible loss of activity. Significantly, this protocol can be extended to nonconventional green heating sources such as microwave and ultrasonic irradiations.

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References

  1. 1.

    J.A. Valderrama, P. Colonelli, D. Vasquez, M.F. Gonzalez, J.A. Rodriguez, C. Theoduloz, Bioorg. Med. Chem. 16, 10172 (2008)

    CAS  Article  Google Scholar 

  2. 2.

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

    CAS  Article  Google Scholar 

  3. 3.

    M.C. Bagley, D.D. Hughes, M.C. Lubinu, E.A. Merrit, P.H. Taylor, N.C.O. Tomkinson, QSAR Comb. Sci. 23, 859 (2004)

    CAS  Article  Google Scholar 

  4. 4.

    X.-T. Li, A.-D. Zhao, L.-P. Moa, Z.-H. Zhang, RSC Adv 4, 51580 (2014)

    CAS  Article  Google Scholar 

  5. 5.

    Y. Zhang, J. Ouyang, H. Yang, Appl. Clay Sci. 95, 252 (2014)

    CAS  Article  Google Scholar 

  6. 6.

    H. Zhu, M.L. Du, M.L. Zou, C.S. Xu, Y.Q. Fu, Dalton Trans. 41, 10465 (2012)

    CAS  Article  Google Scholar 

  7. 7.

    P. Yuan, P.D. Southon, Z. Liu, M.E.R. Green, J.M. Hook, S.J. Antill, C.J. Kepert, J. Phys. Chem. C 112, 15742 (2008)

    CAS  Article  Google Scholar 

  8. 8.

    Y. Zhang, H. Yang, Phys. Chem. Miner. 39, 789 (2012)

    CAS  Article  Google Scholar 

  9. 9.

    X.T. Cao, A.M. Showkat, D.W. Kim, Y.T. Jeong, J.S. Kim, K.T. Lim, J. Nanosci. Nanotechnol. 15, 8617 (2015)

    CAS  Article  Google Scholar 

  10. 10.

    B. Shi, Y. Li, H. Zhang, W. Wu, R. Ding, J. Dang, J. Wang, J. Membr. Sci. 498, 242 (2016)

    CAS  Article  Google Scholar 

  11. 11.

    H. Bai, H. Zhang, Y. He, J. Liu, B. Zhang, J. Wang, J. Membr. Sci. 454, 220 (2014)

    CAS  Article  Google Scholar 

  12. 12.

    R.S. Murali, M. Padaki, T. Matsuura, M.S. Abdullah, A.F. Ismail, Sep. Purif. Technol. 132, 187 (2014)

    Article  Google Scholar 

  13. 13.

    Y. Ren, B. Liu, Z. Zhang, J. Lin, J. Ind. Eng. Chem. 21, 1127 (2015)

    CAS  Article  Google Scholar 

  14. 14.

    B. Yang, J.J. Pignatello, D. Qu, B. Xing, J. Phys. Chem. A 119, 1055 (2015)

    CAS  Article  Google Scholar 

  15. 15.

    S. Sadjadi, M.M. Heravi, Curr. Org. Chem. 20, 1404 (2016)

    CAS  Article  Google Scholar 

  16. 16.

    S.H. Teo, M. Goto, Y.H. Taufiq-Yap, J. Supercrit. Fluids 104, 243 (2015)

    CAS  Article  Google Scholar 

  17. 17.

    A. Escobar, A. Sathicq, L. Pizzio, M. Blanco, G. Romanelli, Process Saf. Environ. Prot. 98, 176 (2015)

    CAS  Article  Google Scholar 

  18. 18.

    H. Eshghi, A. Javid, A. Khojastehnezhad, F. Moeinpour, F.F. Bamoharram, M. Bakavoli, M. Mirzaei, Chin. J. Catal. 36, 299 (2015)

    CAS  Article  Google Scholar 

  19. 19.

    M.S. Tiwari, G.D. Yadav, Chem. Eng. J. 266, 64 (2015)

    CAS  Article  Google Scholar 

  20. 20.

    K. Pamin, M. Pronczuk, S. Basąg, W. Kubiak, Z. Sojka, J. Połtowicz, Inorg. Chem. Commun. 59, 13 (2015)

    CAS  Article  Google Scholar 

  21. 21.

    L. Hong, Y. Gui, J. Lu, J. Hu, J. Yuan, L. Niu, Int. J. Hydrogen Energy 38, 11074 (2013)

    CAS  Article  Google Scholar 

  22. 22.

    Y. Zhu, M. Zhu, L. Kang, F. Yu, B. Dai, Ind. Eng. Chem. Res. 54, 2040–2047 (2015)

    CAS  Article  Google Scholar 

  23. 23.

    J.J. Walsh, A.M. Bond, R.J. Forster, T.E. Keyes, Coord. Chem. Rev. 306, 217 (2016)

    CAS  Article  Google Scholar 

  24. 24.

    J.H. Choi, T.H. Kang, Y. Bang, J.H. Song, I.K. Song, Catal. Commun. 55, 29 (2014)

    CAS  Article  Google Scholar 

  25. 25.

    S.-S. Wang, G.-Y. Yang, Chem. Rev. 115, 4893 (2015)

    CAS  Article  Google Scholar 

  26. 26.

    J. Xiong, W. Zhu, W. Ding, L. Yang, Y. Chao, H. Li, F. Zhu, H. Li, Ind. Eng. Chem. Res. 53, 19895 (2014)

    CAS  Article  Google Scholar 

  27. 27.

    E. Rafiee, F. Mirnezami, J. Mol. Liq. 199, 156 (2014)

    CAS  Article  Google Scholar 

  28. 28.

    M.M. Heravi, S. Sadjadi, H.A. Oskooie, R.H. Shoar, F.F. Bamoharram, Tetrahedron Lett. 50, 662 (2009)

    CAS  Article  Google Scholar 

  29. 29.

    M.M. Heravi, S. Sadjadi, N.M. Haj, H.A. Skooief, F. Bamoharram, Catal. Commun. 10, 1643 (2009)

    CAS  Article  Google Scholar 

  30. 30.

    M.M. Heravi, M. Saeedi, Y.S. Beheshtiha, H.A. Oskooie, Mol. Divers. 15, 239 (2011)

    CAS  Article  Google Scholar 

  31. 31.

    P. Djomgoue, D. Njopwouo, J. Surf. Eng. Mater. Adv. Technol. 3, 275 (2013)

    Google Scholar 

  32. 32.

    S. Bordeepong, D. Bhongsuwan, T. Pungrassami, T. Bhongsuwan, Songklanakarin J. Sci. Technol. 33, 599 (2011)

    CAS  Google Scholar 

  33. 33.

    S. Mallik, S.S. Dash, K.M. Parida, B.K. Mohapatra, J. Colloid Interface Sci. 300, 237 (2006)

    CAS  Article  Google Scholar 

  34. 34.

    S. Dastkhoon, Z. Tavakoli, S. Khodabakhshi, M. Baghernejad, M.K. Abbasabadi, New J. Chem. 39, 7268 (2015)

    CAS  Article  Google Scholar 

  35. 35.

    S. Khodabakhshi, A. Rashidi, Z. Tavakoli, M. Baghernejad, A. Yadegari, Monatsh. Chem. 147, 791 (2016)

    CAS  Article  Google Scholar 

  36. 36.

    A. Ganesan, J. Kothandapani, S.G. Subramaniapillai, RSC Adv. 6, 20582 (2016)

    CAS  Article  Google Scholar 

Download references

Acknowledgments

The authors appreciate partial financial supports from Alzahra University and the Iran Polymer and Petrochemical Institute. MMH is also thankful to the Iran National Science Foundation (INSF).

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Correspondence to Samahe Sadjadi or Majid M. Heravi.

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Sadjadi, S., Heravi, M.M. & Daraie, M. Heteropolyacid supported on amine-functionalized halloysite nano clay as an efficient catalyst for the synthesis of pyrazolopyranopyrimidines via four-component domino reaction. Res Chem Intermed 43, 2201–2214 (2017). https://doi.org/10.1007/s11164-016-2756-8

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Keywords

  • Heteropolyacids
  • Halloysite clay
  • Catalyst
  • Pyrazolopyranopyrimidines