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Application of Fe3O4@SiO2@sulfamic acid magnetic nanoparticles as recyclable heterogeneous catalyst for the synthesis of imine and pyrazole derivatives in aqueous medium

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Abstract

Sulfamic acid supported on Fe3O4@SiO2 superpara magnetic nanoparticles was successfully applied as a recyclable solid acid catalyst with a large density of sulfamic acid groups for the synthesis of pyrazole derivatives, an important class of potentially bioactive compounds. The products are obtained in high yield from the one-pot reaction procedure involving dicarbonyl compounds and hydrazines/hydrazides. This new method totally avoids the use of toxic or expensive solvents and organic acids in this reaction.

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References

  1. J. Ying, R.M. Lee, P.S. Williams, J.C. Jeffrey, S.F. Sherif, B. Brian, Z. Maciej, Biotechnol. Bioeng. 96, 1139 (2007)

    Article  Google Scholar 

  2. J. Lee, Y. Jun, S. Yeon, J. Shin, Angew. Chem. Int. Ed. 45, 8160 (2006)

    Article  CAS  Google Scholar 

  3. N. Tobias, S. Bernhard, H. Heinrich, H. Margarete, V.R. Brigitte, J. Magn. Mater. 293, 483 (2005)

    Article  Google Scholar 

  4. H. Gu, K. Xu, C. Xu, B. Xu, Chem. Commun. 9, 941 (2006)

    Article  Google Scholar 

  5. I. Akira, T. Kouji, K. Kazuyoshi, S. Masashige, H. Hiroyuki, M. Kazuhiko, S. Toshiaki, K. Takeshi, Cancer Sci. 94, 308 (2003)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  7. S. Shylesh, V. Schunemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  9. M. Gawande, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 3371 (2013)

    Article  CAS  Google Scholar 

  10. M.B. Gawande, P.S. Branco, I.D. Nogueira, C.A.A. Ghumman, N. Bundaleski, A. Santos, O.M.N.D. Teodoro, R. Luque, Green Chem. 15, 682 (2013)

    Article  CAS  Google Scholar 

  11. M.B. Gawande, A.K. Rathi, P.S. Branco, I.D. Nogueira, A. Velhinho, J.J. Shrikhande, U.U. Indulkar, R.V. Jayaram, C.A.A. Ghumman, N. Bundaleski, O.M.N.D. Teodoro, Chem. Eur. J. 18, 12628 (2012)

    Article  CAS  Google Scholar 

  12. M.B. Gawande, A.K. Rathi, I.D. Nogueira, C.A.A. Ghumman, N. Bundaleski, O.M.N.D. Teodoro, ChemPlusChem. 77, 865 (2012)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. M.B. Gawande, R. Luque, R. Zboril, ChemCatChem. 6, 3312 (2014)

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. R. Linhardt, Q.M. Kainz, R.N. Grass, W.J. Stark, O. Reiser, RSC Adv. 4, 8541 (2014)

    Article  CAS  Google Scholar 

  17. S. Fernandes, C.M. Eichenseer, P. Kreitmeier, J. Rewitzer, V. Zlateski, R.N. Grass, W.J. Stark, O. Reiser, RSC Adv. 5, 46430 (2015)

    Article  CAS  Google Scholar 

  18. A. Schätz, R.N. Grass, Q. Kainz, W.J. Stark, O. Reiser, Chem. Mater. 22, 305 (2010)

    Article  Google Scholar 

  19. M.B. Gawande, V.D.B. Bonifácio, R. Luque, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 5522 (2013)

    Article  CAS  Google Scholar 

  20. M.B. Gawande, A.K. Rathi, P.S. Branco, R.S. Varma, Appl. Sci. 3, 656 (2013)

    Article  CAS  Google Scholar 

  21. C.J. Li, L. Chen, Chem. Soc. Rev. 5, 68 (2006)

    Article  Google Scholar 

  22. C.J. Li, Chem. Rev. 105, 3095 (2005)

    Article  CAS  Google Scholar 

  23. C.J. Li, Chem. Rev. 93, 2023 (1993)

    Article  CAS  Google Scholar 

  24. N. Mei, B. Liu, J. Zheng, K. Lv, D. Tang, Z. Zhang, Catal. Sci. Technol. 5, 3194 (2015)

    Article  CAS  Google Scholar 

  25. B. Liu, Y. Ren, Z. Zhang, Green Chem. 17, 1610 (2015)

    Article  CAS  Google Scholar 

  26. Z. Zhang, J. Zhen, B. Liu, K. Lv, K. Deng, Green Chem. 17, 1308 (2015)

    Article  CAS  Google Scholar 

  27. Sh Wang, Z. Zhang, B. Liu, ACS Sustain. Chem. Eng. 3, 406 (2015)

    Article  CAS  Google Scholar 

  28. Z. Zhang, Z. Yuan, D. Tang, Y. Ren, K. Lv, B. Liu, ChemSusChem. 7, 3496 (2014)

    Article  CAS  Google Scholar 

  29. Sh Yin, J. Sun, B. Liu, Z. Zhang, J. Mater. Chem. A. 3, 4992 (2015)

    Article  CAS  Google Scholar 

  30. R. Abu-Reziq, H. Alper, D.S. Wang, M.L. Post, J. Am. Chem. Soc. 128, 5279 (2006)

    Article  CAS  Google Scholar 

  31. G. Chouhan, D.S. Wang, H. Alper, Chem. Commun. 45, 4809 (2007)

    Article  Google Scholar 

  32. T. Hara, T. Kaneta, K. Mori, T. Mitsudome, T. Mizugaki, K. Ebitani, K. Kaneda, Green Chem. 9, 1246 (2007)

    Article  CAS  Google Scholar 

  33. M.J. Jin, D.H. Lee, Angew. Chem. Int. Ed. 49, 1119 (2010)

    Article  CAS  Google Scholar 

  34. E. Rafiee, S. Eavani, Green Chem. 13, 2116 (2011)

    Article  CAS  Google Scholar 

  35. F.P. Ma, P.H. Li, B.L. Li, L.P. Mo, N. Liu, H.J. Kang, Y.N. Liu, Z.H. Zhang, Appl. Catal. A. Gen. 457, 34 (2013)

    Article  CAS  Google Scholar 

  36. Y.H. Liu, J. Deng, J.W. Gao, Z.H. Zhang, Adv. Synth. Catal. 354, 441 (2012)

    Article  CAS  Google Scholar 

  37. R.B.N. Baig, R.S. Varma, Green Chem. 15, 398 (2013)

    Article  Google Scholar 

  38. J. Deng, L.P. Mo, F.Y. Zhao, L.L. Hou, L. Yang, Z.H. Zhang, Green Chem. 13, 2576 (2011)

    Article  CAS  Google Scholar 

  39. C.Ó. Dálaigh, S.A. Corr, Y. Gun’ko, S.J. Connon, Angew. Chem. Int. Ed. 46, 4329 (2007)

    Article  Google Scholar 

  40. Y. Zhang, C.G. Xia, Appl. Catal. A. Gen. 366, 141 (2009)

    Article  CAS  Google Scholar 

  41. X.X. Zheng, S.Z. Luo, L. Zhang, J.P. Cheng, Green Chem. 11, 455 (2009)

    Article  CAS  Google Scholar 

  42. J. Lee, Y. Lee, J.K. Youn, H.B. Na, T. Yu, H. Kim, S.M. Lee, Y.M. Koo, J.H. Kwak, H.G. Park, H.N. Chang, M. Hwang, J.G. Park, J. Kim, T. Hyeon, Small 4, 143 (2008)

    Article  CAS  Google Scholar 

  43. R. Katritzky, C. W. Rees, E. F. Scriven, J, Comprehensive Heterocyclic Chemistry (Pergamon Press: Oxford, 5, 1996)

  44. R. Lin, G. Chiu, Y. Yu, P.J. Connolly, S. Li, Y. Lu, M. Adams, A.R. Fuentes-Pesquera, S.L. Emanuel, L.M. Greenberger, Bioorg. Med. Chem. Lett. 17, 4557 (2007)

    Article  CAS  Google Scholar 

  45. N. Gokhan-Kelekci, S. Yabanoglu, E. Kupeli, U. Salgin, O. Ozgen, G. Ucar, E. Yesilada, E. Kendi, A.A. Yesilada, Bioorg. Med. Chem. 15, 5775 (2007)

    Article  Google Scholar 

  46. M. Barcelo, E. Ravin, C.F. Masaguer, E. Domínguez, F.M. Areias, J. Brea, M.I. Loza, Bioorg. Med. Chem. Lett. 17, 4873 (2007)

    Article  CAS  Google Scholar 

  47. M.A. Nasseri, B. Zakerinasab, M.M. Samieadel, RSC Adv. 4, 41753 (2014)

    Article  CAS  Google Scholar 

  48. M.A. Nasseri, F. Kamali, B. Zakerinasab, RSC Adv. 5, 26517 (2015)

    Article  CAS  Google Scholar 

  49. M.A. Nasseri, F. Ahrari, B. Zakerinasab, RSC Adv. 5, 13901 (2015)

    Article  CAS  Google Scholar 

  50. M.A. Nasseri, S.A. Alavi, B. Zakerinasab, J. Iran. Chem. Soc. 10, 21 (2013)

    Article  Google Scholar 

  51. M.A. Nasseri, M. Salimi, Lett. Org. Chem. 10, 164 (2013)

    Article  CAS  Google Scholar 

  52. M.A. Nasseri, S.M. Sadeghzadeh, J. Iran. Chem. Soc. 11, 27 (2014)

    Article  CAS  Google Scholar 

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Acknowledgment

We gratefully acknowledge the support of this work by the Birjand University Research Council.

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Correspondence to B. Zakerinasab.

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Zakerinasab, B., Nasseri, M.A., Hassani, H. et al. Application of Fe3O4@SiO2@sulfamic acid magnetic nanoparticles as recyclable heterogeneous catalyst for the synthesis of imine and pyrazole derivatives in aqueous medium. Res Chem Intermed 42, 3169–3181 (2016). https://doi.org/10.1007/s11164-015-2204-1

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