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Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives

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Abstract

A simple, efficient, and environmentally benign protocol for the synthesis of polyhydroquinoline derivatives was developed using a bio-compatible, heterogeneous, and recoverable mesoporous ionic liquid supported nanoporous silica as a nano-catalyst. The polyhydroquinoline derivatives were obtained by the four-component reaction of aldehyde, Meldrum’s acid, dimedone, and ammonium acetate in excellent yields .

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References

  1. S. Stolte, M. Matzke, J. Arning, A. Boschen, W.-R. Pitner, U. Welz-Biermann, B. Jastorff, J. Ranke, Green Chem. 9, 1170 (2007). doi:10.1039/B711119C

    Article  CAS  Google Scholar 

  2. J. Ranke, S. Stolte, R. Störmann, J. Arning, B. Jastorff, Chem. Rev. 107, 2183 (2007). doi:10.1021/cr050942s

    Article  CAS  Google Scholar 

  3. V.I. Pârvulescu, C. Hardacre, Chem. Rev. 107, 2615 (2007). doi:10.1021/cr050948h

    Article  Google Scholar 

  4. A.M. da Costa Lopes, K.G. João, D.F. Rubik, E. Bogel-Łukasik, L.C. Duarte, J. Andreaus, R. Bogel-Łukasik, Bioresour. Technol. 142, 198 (2013). doi:10.1016/j.biortech.2013.05.032

    Article  Google Scholar 

  5. M. Valkenberg, W. Hölderich, Green Chem. 4, 88 (2002). doi:10.1039/b107946h

    Article  CAS  Google Scholar 

  6. C.P. Mehnert, Chem. A Eur. J. 11, 50 (2005). doi:10.1002/chem.200400683

    Article  Google Scholar 

  7. D.J. Macquarrie, Chem. Commun. (1997). doi:10.1039/A700261K

    Google Scholar 

  8. C. Paun, J. Barklie, P. Goodrich, H.Q.N. Gunaratne, A. McKeown, V.I. Pârvulescu, C. Hardacre, J. Mol. Catal. A: Chem. 269, 64 (2007). doi:10.1016/j.molcata.2007.01.002

    Article  CAS  Google Scholar 

  9. R. Janis, P. Silver, D. Triggle, Adv. Drug Res. 16, 309 (1987)

    CAS  Google Scholar 

  10. R.A. Janis, D.J. Triggle, J. Med. Chem. 26, 775 (1983). doi:10.1021/jm00360a001

    Article  CAS  Google Scholar 

  11. F. Bossert, W. Vater, Med. Res. Rev. 9, 291 (1989). doi:10.1002/med.2610090304

    Article  CAS  Google Scholar 

  12. T. Godfraid, R. Miller, M. Wibo, Pharmocol. Rev. 38, 321 (1986)

    Google Scholar 

  13. A. Sausins, G. Duburs, Heterocycles 27, 291 (1988). doi:10.3987/REV-87-371

    Article  CAS  Google Scholar 

  14. P. Mager, R. Coburn, A. Solo, D. Triggle, H. Rothe, Drug Des. Discov. 8, 273 (1992)

    CAS  Google Scholar 

  15. R. Mannhold, B. Jablonka, W. Voigt, K. Schönafinger, E. Schraven, Eur. J. Med. Chem. 27, 229 (1992). doi:10.1016/0223-5234(92)90006-m

    Article  CAS  Google Scholar 

  16. G. Mohammadi Ziarani, S. Asadi, A. Badiei, S. Mousavi, P. Gholamzadeh, Res. Chem. Intermed. 41, 637 (2015). doi:10.1007/s11164-013-1217-x

    Article  Google Scholar 

  17. P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, Z. Bahrami, Eur. J. Org. Chem. 3, 279 (2012). doi:10.5155/eurjchem.3.3.279-282.630

    Article  CAS  Google Scholar 

  18. G. Mohammadi Ziarani, A. Badiei, A. Abbasi, Z. Farahani, Chin. J. Chem. 27, 1537 (2009). doi:10.1002/cjoc.200990259

    Article  Google Scholar 

  19. A. Badiei, H. Goldooz, G. Mohammadi Ziarani, Appl. Surf. Sci. 257, 4912 (2011). doi:10.1016/j.apsusc.2010.12.146

    Article  CAS  Google Scholar 

  20. S. Hamoudi, A. El-Nemr, K. Belkacemi, J. Colloid Interface Sci. 343, 615 (2010). doi:10.1016/j.jcis.2009.11.070

    Article  CAS  Google Scholar 

  21. T. Sasaki, C. Zhong, M. Tada, Y. Iwasawa, Chem. Commun. (2005). doi:10.1039/B500349K

    Google Scholar 

  22. D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024 (1998). doi:10.1021/ja974025i

    Article  CAS  Google Scholar 

  23. K. Sing, D. Everett, R. Haul, L. Moscou, R. Peirotti, J. Rouquerol, Pure Appl. Chem. 57, 603 (1985)

    Article  CAS  Google Scholar 

  24. G. Socrates, Infrared and Raman Characteristic Group Frequencies (Wiley, London, 2004)

    Google Scholar 

  25. X.S. Fan, Y.Z. Li, X.Y. Zhang, G.R. Qu, J.J. Wang, X.Y. Hu, Heteroat. Chem. 17, 382 (2006). doi:10.1002/hc.20221

    Article  CAS  Google Scholar 

  26. S. Tu, Q. Wei, H. Ma, D. Shi, Y. Gao, G. Cui, Synth. Commun. 31, 2657 (2001). doi:10.1081/scc-100105393

    Article  CAS  Google Scholar 

  27. M. Suárez, E. Ochoa, Y. Verdecia, B. Pita, L. Morán, N. Martín, M. Quinteiro, C. Seoane, J. Soto, H. Novoa, N. Blaton, O.M. Peters, Tetrahedron 55, 875 (1999). doi:10.1016/s0040-4020(98)01078-3

    Article  Google Scholar 

  28. J. Svetlik, V. Hanus, J. Bella, Synth. Commun. 23, 631 (1993). doi:10.1080/00397919308009821

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of Alzahra University and the University of Tehran.

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Authors and Affiliations

  1. Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran

    Ghodsi Mohammadi Ziarani, Leila Seyedakbari & Shima Asadi

  2. School of Chemistry, College of Science, University of Tehran, Tehran, Iran

    Alireza Badiei & Marzieeh Yadavi

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  1. Ghodsi Mohammadi Ziarani
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  2. Leila Seyedakbari
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  3. Shima Asadi
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  4. Alireza Badiei
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Correspondence to Ghodsi Mohammadi Ziarani.

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Mohammadi Ziarani, G., Seyedakbari, L., Asadi, S. et al. Ionic liquid supported nanoporous silica (SBA-IL) as an efficient and heterogeneous catalyst in the domino synthesis of polyhydroquinoline derivatives. Res Chem Intermed 42, 499–509 (2016). https://doi.org/10.1007/s11164-015-2036-z

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  • DOI: https://doi.org/10.1007/s11164-015-2036-z

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