Journal of the Iranian Chemical Society

, Volume 15, Issue 12, pp 2811–2819 | Cite as

Practical and efficient synthesis of tetrahydrobenzo[b]pyran using caffeine supported on silica as an ionic liquid solid acid catalyst

  • Mohammad BakheradEmail author
  • Ali Keivanloo
  • Elmira Moradian
  • Amir H. Amin
  • Rahele Doosti
  • Mahsa Armaghan
Original Paper


The new catalyst silica-caffeine hydrogen sulfate [SiO2-caff.]HSO4 was conveniently prepared from commercially available 3-chloropropyltriethoxysilane via immobilization on silica followed by reaction with caffeine. The catalyst prepared was then characterized by the FT-IR spectroscopy, TGA, EDX, and SEM techniques. It was found that this heterogeneous catalyst was a highly efficient one for the synthesis of tetrahydrobenzo[b]pyrans in good-to-high yields, and could be recovered by a simple filtration of the reaction solution and reused for five consecutive runs. The attractive features of this method are simple procedure, clean reaction, easy work-up, use of a reusable catalyst, and performing a multi-component reaction.


Ionic liquid solid acid Reusable catalyst Tetrahydrobenzo[b]pyran 



We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

Supplementary material

13738_2018_1468_MOESM1_ESM.docx (2.8 mb)
Supplementary material 1 (DOCX 2872 KB)


  1. 1.
    M. Baghernejad, K. Niknam, Inter. J. Chem. 4, 52 (2012)CrossRefGoogle Scholar
  2. 2.
    K. Niknam, A. Piran, Green Sus. Chem. 3, 1 (2013)CrossRefGoogle Scholar
  3. 3.
    F. Shirini, M. Seddighi, M. Mazloumi, M. Makhsous, M. Abedini, J. Mol. Liq. 208, 291 (2015)CrossRefGoogle Scholar
  4. 4.
    A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, J. Mol. Liq. 211, 373 (2015)CrossRefGoogle Scholar
  5. 5.
    M. Seddighi, F. Shirini, M. Mamaghani, C. R. Chim. 18, 573 (2015)CrossRefGoogle Scholar
  6. 6.
    K. Niknam, A. Piran, Z. Karimi, J. Iran. Chem. Soc. 13, 859 (2016)CrossRefGoogle Scholar
  7. 7.
    N.G. Khaligh, J. Mol. Catal. A Chem. 349, 63 (2011)CrossRefGoogle Scholar
  8. 8.
    A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaniniejad, A.A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq. 167, 69 (2012)CrossRefGoogle Scholar
  9. 9.
    M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A Gen. 400, 1365 (2011)CrossRefGoogle Scholar
  10. 10.
    M. Nouri Sefat, D. Saberi, K. Niknam, Catal. Lett. 141, 1713 (2011)CrossRefGoogle Scholar
  11. 11.
    A. Chrobok, S. Baj, W. Pudlo, A. Jarzebski, Appl. Catal. A 366, 22 (2009)CrossRefGoogle Scholar
  12. 12.
    J.M. Xu, B.K. Liu, W.B. Wu, C. Qian, Q. Wu, X.F. Lin, J. Org. Chem. 71, 3991 (2006)CrossRefGoogle Scholar
  13. 13.
    C. Paun, J. Barklie, P. Goodrich, H. Gunaratne, A. McKeown, V. Parvulescu, C. Hardacre, J. Mol. Catal. A Chem. 269, 64 (2007)CrossRefGoogle Scholar
  14. 14.
    K. Qiao, H. Hagiwara, C. Yokoyama, J. Mol. Catal. A Chem. 246, 65 (2006)CrossRefGoogle Scholar
  15. 15.
    R. Sugimara, K. Qiao, D. Tomida, C. Yokoyama, Catal. Commun. 8, 770 (2007)CrossRefGoogle Scholar
  16. 16.
    A.A. Hassanien, M.A. Zahrran, M.S.A. El-Gaby, M.M. Ghorab, J. Indian Chem. Soc. 76, 350 (1999)Google Scholar
  17. 17.
    K. Niknam, N. Borazjani, R. Rashidian, A. Jamli, Chin. J. Catal. 34, 2245 (2013)CrossRefGoogle Scholar
  18. 18.
    K. Niknam, M. Khataminejad, F. Zeyaei, Tetrahedron Lett. 57, 361 (2016)CrossRefGoogle Scholar
  19. 19.
    S. Gao, C.H. Tsai, C. Tseng, C.-F. Yao, Tetrahedron 64, 9143 (2008)CrossRefGoogle Scholar
  20. 20.
    S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)CrossRefGoogle Scholar
  21. 21.
    N. Zohreh, S.H. Hosseini, A. Pourjavadi, C. Bennett, RSC Adv. 4, 50047 (2014)CrossRefGoogle Scholar
  22. 22.
    B. Paplal, S. Nagaraju, P. Veerabhadraiah, K. Sujatha, S. Kanvah, B.V. Kumar, D. Kashinath, RSC Adv. 4, 54168 (2014)CrossRefGoogle Scholar
  23. 23.
    J. Schütz, W.A. Herrmann, J. Organomet. Chem. 689, 2995 (2004)CrossRefGoogle Scholar
  24. 24.
    F.T. Luo, H.K. Lo, J. Organomet. Chem. 696, 1262 (2011)CrossRefGoogle Scholar
  25. 25.
    M. Bakherad, R. Doosti, M. Mirzaee, K. Jadidi, Iran. J. Catal. 7, 27 (2017)Google Scholar
  26. 26.
    M.A.P. Martins, C.P. Frizzo, D.N. Moreira, L. Buriol, P. Machado, Chem. Rev. 109, 4140 (2009)CrossRefGoogle Scholar
  27. 27.
    R. Kumar, K. Raghuvanshi, R.K. Verma, M.S. Singh, Tetrahedron Lett. 51, 5933 (2010)CrossRefGoogle Scholar
  28. 28.
    F. Adam, H. Osman, K.M. Hello, J. Coll. Inter. Sci. 331, 143 (2009)CrossRefGoogle Scholar
  29. 29.
    H.R. Safaei, M. Shekouhy, S. Rahmanpur, A. Shirinfeshan, Green Chem. 14, 1696 (2012)CrossRefGoogle Scholar
  30. 30.
    O.H. Qareaghaj, S. Mashkouri, M.R. Naimi-Jamal, G. Kaupp, RSC Adv. 4, 48191 (2014)CrossRefGoogle Scholar
  31. 31.
    O. Rosati, A. Pelosi, A. Temperini, V. Pace, M. Curini, Synthesis 48, 1533 (2016)CrossRefGoogle Scholar
  32. 32.
    A. T. Khan, M. Lal, S. Ali, M.M. Khan, Tetrahedron Lett. 52, 5327 (2011)CrossRefGoogle Scholar
  33. 33.
    M.G. Ahmed, U. Romman, K. Akhter, K. Jahan, M.N.H. Bhuiyan, M.E. Halim, Synth. Commun. 41, 2822 (2011)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2018

Authors and Affiliations

  1. 1.School of ChemistryShahrood University of TechnologyShahroodIran
  2. 2.Chemistry Department, Science and Research BranchIslamic Azad UniversityTehranIran

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