Skip to main content

Atom-economy click synthesis of tetrahydrobenzo[b]pyrans using carbon-based solid acid as a novel, highly efficient and reusable heterogeneous catalyst


Carbon-based solid acid has been used as a mild and efficient heterogeneous catalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives via a one-vessel, three-component cyclocondensation of dimedone, aryl aldehydes, and malononitrile with high atom economy ranging from 94.2 to 95.4 %. The remarkable features of this new method are short reaction times, high yields, clean reaction profiles, and simple work-up procedure. The reactions were performed in ethanol and the catalyst could be recycled after a simple work-up, and used for many runs without significant loss of its activity. However, using aliphatic aldehydes, moderate yields of the products were obtained. The structure of the catalyst was confirmed by FT-IR spectroscopy, energy dispersive X-ray, X-ray diffraction, and the N2 adsorption/desorption analysis techniques.

This is a preview of subscription content, access via your institution.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2


  1. 1.

    L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)

    CAS  Article  Google Scholar 

  2. 2.

    G.R. Green, J.M. Evans, A.K. Vong, in Comprehensive Heterocyclic Chemistry II, ed. by A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Pergamon, Oxford, 1995), pp. 469–500

    Google Scholar 

  3. 3.

    K. Rehse, W. Schinkel, Arch. Pharm. 316, 988 (1983)

    CAS  Article  Google Scholar 

  4. 4.

    I. Fatima, R. Saxena, G. Kharkwal, M.K. Hussain, N. Yadav, K. Hajela, P.L. Sankhwar, A. Dwivedi, J. Steroid Biochem. Mol. Biol. 138, 123 (2013)

    CAS  Article  Google Scholar 

  5. 5.

    A.E.F.G. Hammam, O.I. Abd El-Salam, A.M. Mohamed, N.A. Hafez, Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem. 44, 1887 (2005)

    Google Scholar 

  6. 6.

    D. Armetso, W.M. Horspool, N. Martin, A. Ramos, C. Seoane, J. Org. Chem. 54, 5190 (1989)

    Google Scholar 

  7. 7.

    S. Hatakeyama, N. Ochi, H. Numata, S. Takano, J. Chem. Soc. Chem. Commun. 1202 (1988)

  8. 8.

    C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana, PCT Int. Appl. WO Patent 200075123. Chem. Abstr. 134, 29313a (2001)

    Google Scholar 

  9. 9.

    S. Paul, S. Ghosh, P. Bhattacharyya, A.R. Das, RSC Adv. 3, 14254 (2013)

    CAS  Article  Google Scholar 

  10. 10.

    M. Amirnejad, M.R. Naimi-Jamal, H. Tourani, H. Ghafuri, Monatsh. Chem. 144, 1219 (2013)

    CAS  Article  Google Scholar 

  11. 11.

    R.S. Bhosale, C.V. Magar, K.S. Solanke, S.B. Mane, S.S. Choudhary, R.P. Pawar, Synth. Commun. 37, 4353 (2007)

    CAS  Article  Google Scholar 

  12. 12.

    J.T. Li, W.Z. Xu, L.C. Yang, T.S. Li, Synth. Commun. 34, 4565 (2004)

    CAS  Article  Google Scholar 

  13. 13.

    J. Zheng, Y. Li, Mendeleev Commun. 21, 280 (2011)

    CAS  Article  Google Scholar 

  14. 14.

    S. Rathod, B. Arbad, M. Lande, Chin. J. Catal. 31, 631 (2010)

    CAS  Article  Google Scholar 

  15. 15.

    M. Hosseini-Sarvari, S. Shafiee-Haghighi, Chem. Heterocycl. Compd. 48, 1307 (2012)

    CAS  Article  Google Scholar 

  16. 16.

    P. Bhattacharyya, K. Pradhan, S. Paul, A.R. Das, Tetrahedron Lett. 53, 4687 (2012)

    CAS  Article  Google Scholar 

  17. 17.

    S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C. R. Chim. 15, 394 (2012)

    CAS  Article  Google Scholar 

  18. 18.

    S. Gurumurthi, V. Sundari, R. Valliappan, E. J. Chem. 6, S466 (2009)

    CAS  Article  Google Scholar 

  19. 19.

    R. Hekmatshoar, S. Majedi, Kh Bakhtiari, Catal. Commun. 9, 307 (2008)

    CAS  Article  Google Scholar 

  20. 20.

    D. Tahmassebi, J.A. Bryson, S.I. Binz, Synth. Commun. 41, 2701 (2011)

    CAS  Article  Google Scholar 

  21. 21.

    Y. Li, B. Du, X. Wang, D. Shi, S. Tu, J. Heterocycl. Chem. 43, 685 (2006)

    CAS  Article  Google Scholar 

  22. 22.

    S. Khaksar, A. Rouhollahpour, S. Mohammadzadeh Talesh, J. Fluorine Chem. 141, 11 (2012)

    CAS  Article  Google Scholar 

  23. 23.

    V.S. Gerard, F. Notheisz, Heterogeneous Catalysis in Organic Chemistry (Elsevier, San Diego, 2000)

    Google Scholar 

  24. 24.

    K. Wilson, J.H. Clark, Pure Appl. Chem. 72, 1313 (2000)

    CAS  Article  Google Scholar 

  25. 25.

    N. Seifi, M.H. Zahedi-Niaki, M.R. Barzegari, A. Davoodnia, R. Zhiani, A.A. Kaju, J. Mol. Catal. A Chem. 260, 77 (2006)

    CAS  Article  Google Scholar 

  26. 26.

    M. Zeinali-Dastmalbaf, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, A. Khojastehnezhad, H.A. Zamani, Bull. Korean Chem. Soc. 32, 656 (2011)

    CAS  Article  Google Scholar 

  27. 27.

    A. Davoodnia, M. Bakavoli, R. Moloudi, M. Khashi, N. Tavakoli-Hoseini, Chin. Chem. Lett. 21, 1 (2010)

    CAS  Article  Google Scholar 

  28. 28.

    N. Tavakoli-Hoseini, A. Davoodnia, Asian J. Chem. 22, 7197 (2010)

    CAS  Google Scholar 

  29. 29.

    A. Davoodnia, A. Khojastehnezhad, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 2243 (2011)

    CAS  Article  Google Scholar 

  30. 30.

    A. Davoodnia, Synth. React. Inorg. Met-Org. Nano-Met. Chem. 42, 1022 (2012)

    CAS  Article  Google Scholar 

  31. 31.

    N. Mohammadzadeh-Dehsorkh, A. Davoodnia, N. Tavakoli-Hoseini, M. Moghaddas, Synth. React. Inorg. Met-Org. Nano-Met. Chem. 41, 1135 (2011)

    CAS  Article  Google Scholar 

  32. 32.

    A. Davoodnia, A. Zare-Bidaki, H. Behmadi, Chin. J. Catal. 33, 1797 (2012)

    CAS  Article  Google Scholar 

  33. 33.

    M. Hara, T. Yoshida, A. Takagaki, T. Takata, J.N. Kondo, S. Hayashi, K. Domen, Angew. Chem. Int. Ed. 43, 2955 (2004)

    CAS  Article  Google Scholar 

  34. 34.

    A. Davoodnia, A. Tavakoli-Nishaburi, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 32, 635 (2011)

    CAS  Article  Google Scholar 

  35. 35.

    M. Moghaddas, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, Chin. J. Catal. 33, 706 (2012)

    CAS  Article  Google Scholar 

  36. 36.

    N. Tavakoli-Hoseini, A. Davoodnia, Chin. J. Chem. 29, 203 (2011)

    CAS  Article  Google Scholar 

  37. 37.

    K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, T. Siemieniewska, Pure Appl. Chem. 57, 603 (1985)

    CAS  Article  Google Scholar 

Download references


The authors express their gratitude to the Islamic Azad University, Mashhad Branch for its financial support.

Author information



Corresponding author

Correspondence to Abolghasem Davoodnia.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Moghaddas, M., Davoodnia, A. Atom-economy click synthesis of tetrahydrobenzo[b]pyrans using carbon-based solid acid as a novel, highly efficient and reusable heterogeneous catalyst. Res Chem Intermed 41, 4373–4386 (2015).

Download citation


  • Carbon-based solid acid
  • Heterogeneous catalysis
  • Reusable catalyst
  • One-vessel reaction
  • Tetrahydrobenzo[b]pyrans