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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Shaabani A, Maleki A, Rezayan AH, Sarvary A (2011) Mol Diversity 15(1):41–68
Mironov MA (2006) QSAR Comb Sci 25(5–6):423–431
Darbarwar M, Sundaramurthy V (1982) Synthesis 1982(5):337–388
Shaabani A, Mohammadpour Amini M, Ghasemi S, Ghadari R, Rezayan AH, Fazaeli Y, Feizi S (2010) Chem Pharm Bull 58(2):270–272
Jin TS, Zhao RQ, Li TS (2006) Arkivoc 11:176–182
Kumar D, Reddy VB, Sharad S, Dube U, Kapur S (2009) Eur J Med Chem 44(9):3805–3809
Li Y, Du B, Wang X, Shi D, Tu S (2006) J Heterocycl Chem 43(3):685–688
Singh K, Singh J, Singh H (1996) Tetrahedron 52(45):14273–14280
Tu S, Gao Y, Guo C (2002) Synth Commun 14:2137–2141
Tu SJ, Miao CB, Gao Y, Feng YJ, Feng JC (2002) Chin J Chem 20(7):703–706
Gao S, Tsai CH, Tseng C, Yao C-F (2008) Tetrahedron 64(38):9143–9149
Bhosale RS, Magar CV, Solanke KS, Mane SB, Choudhary SS, Pawar RP (2007) Synth Commun 37(24):4353–4357
Boumoud B, Yahiaoui A, Boumoud T, Debache A (2012) J Chem Pharm Res 4(1):795–799
Rong L, Li X, Wang H, Shi D, Tu S, Zhuang Q (2006) Synth Commun 36(16):2363–2369
Ziarani GM, Abbasi A, Badiei A, Aslani Z (2010) J Chem 8(1):293–299
Hasaninejad A, Shekouhy M, Golzar N, Zare A, Doroodmand MM (2011) Appl Catal A 402(1–2):11–22
Khan AT, Lal M, Ali S, Khan MM (2011) Tetrahedron Lett 52(41):5327–5332
Hekmatshoar R, Majedi S, Bakhtiari K (2008) Catal Commun 9(2):307–310
Sun WB, Zhang P, Fan J, Chen SH, Zhang ZH (2010) Synth Commun 40(4):587–594
Lian XZ, Huang Y, Li YQ, Zheng WJ (2008) Monatsh Chem 139(2):129–131
Devi I, Bhuyan PJ (2004) Tetrahedron Lett 45(47):8625–8627
Sabitha G, Arundhathi K, Sudhakar K, Sastry B, Yadav J (2009) Synth Commun 39(3):433–442
Balalaie S, Bararjanian M, Sheikh-Ahmadi M, Hekmat S, Salehi P (2007) Synth Commun 37(7):1097–1108
Pore D, Undale K, Dongare B, Desai U (2009) Catal Lett 132(1):104–108
Khodaei MM, Bahrami K, Farrokhi A (2010) Synth Commun 40(10):1492–1499
Balalaie S, Bararjanian M, Amani AM, Movassagh B (2006) Synlett 263–266
Dabiri M, Baghbanzadeh M, Arzroomchilar E (2008) Catal Commun 9(5):939–942
Oskooie HA, Heravi MM, Karimi N, Zadeh ME (2011) Synth Commun 41(3):436–440
Abdollahi-Alibeik M, Pouriayevali M (2012) Catal Commun 22:13–18
Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS (1992) Nature 359(6397):710–712
Ahmed S, Rahman F, Al-Amer A, Al-Mutairi E, Baduruthamal U, Alam K (2012) Reac Kinet Mech Cat 105(2):483–493
Mahendiran C, Maiyalagan T, Vijayan P, Suresh C, Shanthi K (2012) Reac Kinet Mech Cat 105(2):469–481
Zamanifar E, Farzaneh F (2011) Reac Kinet Mech Cat 104(1):197–209
Santhanaraj D, Suresh C, Vijayan P, Venkatathri N, Shanthi K (2010) Reac Kinet Mech Cat 99(2):439–446
Abdollahi-Alibeik M, Pouriayevali M (2011) Reac Kinet Mech Cat 104(1):235–248
Wang R, Li Y, Guo B, Sun H (2011) Energy Fuels 25(9):3940–3949
Abdollahi-Alibeik M, Heidari-Torkabad E (2012) C R Chim 15(6):517–523
Alam M, Sarkar S (2011) Reac Kinet Mech Cat 103(2):493–500
Zhang D, Wang R, Yang X, Yao W (2010) Reac Kinet Mech Cat 101(2):455–463
Balalaie S, Sheikh-Ahmadi M, Bararjanian M (2007) Catal Commun 8(11):1724–1728
Zhao-Qin J, Shun-Jun J, Jun L, Jin-Ming Y (2005) Chin J Chem 23(8):1085–1089
Banerjee S, Horn A, Khatri H, Sereda G (2011) Tetrahedron Lett 52(16):1878–1881
Sing K, Everett D, Haul R, Moscou L, Peirotti R, Rouquerol J (1985) Pure Appl Chem 57:603–619
Sayari A (2000) Angew Chem Int Ed 39(16):2920–2922
Franchi RS, Harlick PJE, Sayari A (2005) Ind Eng Chem Res 44(21):8007–8013
Sayari A, Hamoudi S, Yang Y (2005) Chem Mater 17(1):212–216
Sayari A, Shee D, Al-Yassir N, Yang Y (2010) Top Catal 53(3):154–167
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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