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Synthesis of 4H-benzo[b]pyrans in the presence of sulfated MCM-41 nanoparticles as efficient and reusable solid acid catalyst

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Abstract

A one-pot three-component reaction of various types of aldehydes, dimedone, and malononitrile was studied in the presence of sulfated MCM-41 (SO4 2−/MCM-41) nanoparticles for the synthesis of 4H-benzo[b]pyrans. MCM-41 was synthesized in nanosize by the sol–gel method and then SO4 2−/MCM-41 samples with different calcination temperatures were prepared and characterized by XRD, FT-IR, SEM, and BET techniques. The characterization results show the insertion of sulfate in the mesoporous structure of MCM-41 and the catalytic performance experiments show that SO4 2−/MCM-41 with a calcination temperature of 550 °C has the best catalytic activity. The reusability experiments show that the catalyst is reusable with moderate decrease in activity.

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References

  1. Shaabani A, Maleki A, Rezayan AH, Sarvary A (2011) Mol Diversity 15(1):41–68

    Article  CAS  Google Scholar 

  2. Mironov MA (2006) QSAR Comb Sci 25(5–6):423–431

    Article  CAS  Google Scholar 

  3. Darbarwar M, Sundaramurthy V (1982) Synthesis 1982(5):337–388

    Article  Google Scholar 

  4. Shaabani A, Mohammadpour Amini M, Ghasemi S, Ghadari R, Rezayan AH, Fazaeli Y, Feizi S (2010) Chem Pharm Bull 58(2):270–272

    Article  CAS  Google Scholar 

  5. Jin TS, Zhao RQ, Li TS (2006) Arkivoc 11:176–182

    Google Scholar 

  6. Kumar D, Reddy VB, Sharad S, Dube U, Kapur S (2009) Eur J Med Chem 44(9):3805–3809

    Article  CAS  Google Scholar 

  7. Li Y, Du B, Wang X, Shi D, Tu S (2006) J Heterocycl Chem 43(3):685–688

    Article  CAS  Google Scholar 

  8. Singh K, Singh J, Singh H (1996) Tetrahedron 52(45):14273–14280

    Article  CAS  Google Scholar 

  9. Tu S, Gao Y, Guo C (2002) Synth Commun 14:2137–2141

    Article  Google Scholar 

  10. Tu SJ, Miao CB, Gao Y, Feng YJ, Feng JC (2002) Chin J Chem 20(7):703–706

    Article  CAS  Google Scholar 

  11. Gao S, Tsai CH, Tseng C, Yao C-F (2008) Tetrahedron 64(38):9143–9149

    Article  CAS  Google Scholar 

  12. Bhosale RS, Magar CV, Solanke KS, Mane SB, Choudhary SS, Pawar RP (2007) Synth Commun 37(24):4353–4357

    Article  CAS  Google Scholar 

  13. Boumoud B, Yahiaoui A, Boumoud T, Debache A (2012) J Chem Pharm Res 4(1):795–799

    CAS  Google Scholar 

  14. Rong L, Li X, Wang H, Shi D, Tu S, Zhuang Q (2006) Synth Commun 36(16):2363–2369

    Article  CAS  Google Scholar 

  15. Ziarani GM, Abbasi A, Badiei A, Aslani Z (2010) J Chem 8(1):293–299

    Google Scholar 

  16. Hasaninejad A, Shekouhy M, Golzar N, Zare A, Doroodmand MM (2011) Appl Catal A 402(1–2):11–22

    CAS  Google Scholar 

  17. Khan AT, Lal M, Ali S, Khan MM (2011) Tetrahedron Lett 52(41):5327–5332

    Article  CAS  Google Scholar 

  18. Hekmatshoar R, Majedi S, Bakhtiari K (2008) Catal Commun 9(2):307–310

    Article  CAS  Google Scholar 

  19. Sun WB, Zhang P, Fan J, Chen SH, Zhang ZH (2010) Synth Commun 40(4):587–594

    Article  CAS  Google Scholar 

  20. Lian XZ, Huang Y, Li YQ, Zheng WJ (2008) Monatsh Chem 139(2):129–131

    Article  CAS  Google Scholar 

  21. Devi I, Bhuyan PJ (2004) Tetrahedron Lett 45(47):8625–8627

    Article  CAS  Google Scholar 

  22. Sabitha G, Arundhathi K, Sudhakar K, Sastry B, Yadav J (2009) Synth Commun 39(3):433–442

    Article  CAS  Google Scholar 

  23. Balalaie S, Bararjanian M, Sheikh-Ahmadi M, Hekmat S, Salehi P (2007) Synth Commun 37(7):1097–1108

    Article  CAS  Google Scholar 

  24. Pore D, Undale K, Dongare B, Desai U (2009) Catal Lett 132(1):104–108

    Article  CAS  Google Scholar 

  25. Khodaei MM, Bahrami K, Farrokhi A (2010) Synth Commun 40(10):1492–1499

    Article  CAS  Google Scholar 

  26. Balalaie S, Bararjanian M, Amani AM, Movassagh B (2006) Synlett 263–266

  27. Dabiri M, Baghbanzadeh M, Arzroomchilar E (2008) Catal Commun 9(5):939–942

    Article  CAS  Google Scholar 

  28. Oskooie HA, Heravi MM, Karimi N, Zadeh ME (2011) Synth Commun 41(3):436–440

    Article  CAS  Google Scholar 

  29. Abdollahi-Alibeik M, Pouriayevali M (2012) Catal Commun 22:13–18

    Article  CAS  Google Scholar 

  30. Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS (1992) Nature 359(6397):710–712

    Article  CAS  Google Scholar 

  31. Ahmed S, Rahman F, Al-Amer A, Al-Mutairi E, Baduruthamal U, Alam K (2012) Reac Kinet Mech Cat 105(2):483–493

    Article  CAS  Google Scholar 

  32. Mahendiran C, Maiyalagan T, Vijayan P, Suresh C, Shanthi K (2012) Reac Kinet Mech Cat 105(2):469–481

    Article  CAS  Google Scholar 

  33. Zamanifar E, Farzaneh F (2011) Reac Kinet Mech Cat 104(1):197–209

    Article  CAS  Google Scholar 

  34. Santhanaraj D, Suresh C, Vijayan P, Venkatathri N, Shanthi K (2010) Reac Kinet Mech Cat 99(2):439–446

    CAS  Google Scholar 

  35. Abdollahi-Alibeik M, Pouriayevali M (2011) Reac Kinet Mech Cat 104(1):235–248

    Article  CAS  Google Scholar 

  36. Wang R, Li Y, Guo B, Sun H (2011) Energy Fuels 25(9):3940–3949

    Article  CAS  Google Scholar 

  37. Abdollahi-Alibeik M, Heidari-Torkabad E (2012) C R Chim 15(6):517–523

    Article  CAS  Google Scholar 

  38. Alam M, Sarkar S (2011) Reac Kinet Mech Cat 103(2):493–500

    Article  CAS  Google Scholar 

  39. Zhang D, Wang R, Yang X, Yao W (2010) Reac Kinet Mech Cat 101(2):455–463

    Article  CAS  Google Scholar 

  40. Balalaie S, Sheikh-Ahmadi M, Bararjanian M (2007) Catal Commun 8(11):1724–1728

    Article  CAS  Google Scholar 

  41. Zhao-Qin J, Shun-Jun J, Jun L, Jin-Ming Y (2005) Chin J Chem 23(8):1085–1089

    Article  Google Scholar 

  42. Banerjee S, Horn A, Khatri H, Sereda G (2011) Tetrahedron Lett 52(16):1878–1881

    Article  CAS  Google Scholar 

  43. Sing K, Everett D, Haul R, Moscou L, Peirotti R, Rouquerol J (1985) Pure Appl Chem 57:603–619

    Article  CAS  Google Scholar 

  44. Sayari A (2000) Angew Chem Int Ed 39(16):2920–2922

    CAS  Google Scholar 

  45. Franchi RS, Harlick PJE, Sayari A (2005) Ind Eng Chem Res 44(21):8007–8013

    Article  CAS  Google Scholar 

  46. Sayari A, Hamoudi S, Yang Y (2005) Chem Mater 17(1):212–216

    Article  CAS  Google Scholar 

  47. Sayari A, Shee D, Al-Yassir N, Yang Y (2010) Top Catal 53(3):154–167

    Article  CAS  Google Scholar 

Download references

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Correspondence to Mohammad Abdollahi-Alibeik.

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Abdollahi-Alibeik, M., Nezampour, F. Synthesis of 4H-benzo[b]pyrans in the presence of sulfated MCM-41 nanoparticles as efficient and reusable solid acid catalyst. Reac Kinet Mech Cat 108, 213–229 (2013). https://doi.org/10.1007/s11144-012-0504-7

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  • DOI: https://doi.org/10.1007/s11144-012-0504-7

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