Employing a hydrophobic-bentonite as a highly efficient and versatile catalyst for a green one-pot and rapid synthesis of 4H-benzo-[b]-pyran derivatives

Iranian Journal of Catalysis

مقاله 6، دوره 8، شماره 4، اسفند 2018، صفحه 281-288   

نوع مقاله: Articles

نویسندگان

Mohammad Ebrahim Sedaghat^* ؛ Faranak Farhadi؛ Mohammad Reza Nazarifar؛ Rezvan Sheikhi Kamareji

Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, Iran.

چکیده

A hydrophobic-bentonite catalyst (cetyltrimethyl ammonium bromide-bentonite) has been used as a very mild, neutral, eco-friendly, reusable, non-toxic, low-cost and easily available catalyst. It was prepared by replacing the exchangeable Na⁺ cations of a homoionic Na–bentonite with cetyltrimethyl ammonium bromide (CTMAB) cations. The catalyst was characterized by XRD, BET and SEM. The BET data and XRD patterns showed that the surfactant ions enter the interlayer space of catalyst. In order to study the catalytic properties, we carried out a one-pot practical, efficient and green multicomponent synthesis of 4H-benzo-[b]-pyran derivatives in terms of high yield, simple experimental procedure, low reaction time and simple work-up.

کلیدواژه‌ها

Hydrophobic-bentonite؛ green chemistry؛ Multi-component reactions؛ One-pot synthesis؛ Pyran derivatives

مراجع

[1] M.E. Sedaghat, M. Rajabpour Booshehri, M.R. Nazarifar, F. Farhadi, Appl. Clay Sci. 95 (2014) 55-59.
[2] M.E. Sedaghat, M. Ghiaci, H. Aghaei, S. Soleimanian-Zad, Appl. Clay. Sci. 46 (2009) 125-130.
[3] M.E. Sedaghat, M. Ghiaci, H. Aghaei, S. Soleimanian-Zad, Appl. Clay. Sci. 46 (2009) 131-135.
[4] F.A. Banat, B. Al-Bashir, S. Al-Asheh, O. Hayajneh, Environ. Pollut. 107 (2000) 391-398.
[5] R. Ocampo-Perez, R. Leyva-Ramos, J. Mendoza-Barron, R.M. Guerrero-Coronado, J. Colloid Interface Sci. 364 (2011) 195-204.
[6] M. Ghiaci, Z. Sadeghi, M.E. Sedaghat, H. Karimi-Maleh, J. Safaei-Ghomi, A. Gil, Appl. Catal. 381(2010) 121-131.
[7] M. Ghiaci, M.E. Sedaghat, H. Aghaei, A. Gil, J. Chem. Technol. Biotechnol. 84 (2009) 1908-1915.
[8] M. Ghiaci, H. Aghaei, S. Soleimanian, M.E. Sedaghat, Appl. Clay. Sci. 43 (2009) 289-295.
[9] M. Ghiaci, H. Aghaei, S. Soleimanian, M.E. Sedaghat, Appl. Clay. Sci. 43 (2009) 308-316.
[10] M. Ghiaci, R.J. Kalbasi, M.E. Sedaghat, Org. Process Res. Dev. 7 (2003) 936-938.
[11] M. Ghiaci, M.E. Sedaghat, R.J. Kalbasi, A. Abbaspur, Tetrahedron 61 (2005) 5529-5534.
[12] R.A. Vaia, R.K. Teukolsky, E.P. Giannelis, Chem. Mater. 6 (1994) 1017-1022.
[13] W. Xie, Z. Gao, W. Pan, D. Hunter, A. Singh, R. Vaia, Chem. Mater.13 (2001) 2979-2990.
[14] Y. Li, H. Ishida, Macromolecules 38 (2005) 6513-6519.
[15] L.B. De Paiva, A.R. Morales, F.R.V. Diaz, Appl. Clay Sci. 42 (2008) 8-24.
[16] R.S. Juang, S.H. Lin, K.H. Tsao, J. Colloid Interface Sci. 269 (2004) 46-52.
[17] F. Bergaya, G. Lagaly, Appl. Clay Sci. 19 (2001) 1-3.
[18] L. Wu, L. Liao, G. Lv, F. Qin, Z. Li, Chem. Eng. J. 236 (2014) 306-313.
[19] C.W. Chiu, T.K. Huang, Y.C. Wang, B.G. Alamani, J.J. Lin, Prog. Polym. Sci. 39 (2014) 443-485.
[20] M.R. Nazarifar, Iran. J. Catal. 5 (2015) 351-355.
[21] Z. Karimi-Jaberi, M.R. Nazarifar, B. Pooladian, Chin. Chem. Lett. 23 (2012) 781-784.
[22] Z. Karimi-Jaberi, M.R. Nazarifar, Eur. Chem. Bull. 3 (2014) 512-514.
[23] T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang, T.S.A. Li, Synlett (2004) 871-873.
[24] X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, Synth. Commun. 33 (2003) 119-126.
[25] L. Bonsignoren, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28 (1993) 517-520.
[26] W.O. Foye, Principles of Medicinal Chemistry, T.L. Lemke, D.A. Williams, Eds., 6th Ed., Lippincott Williams & Wilkins, Philadelphia, 2008.
[27] L.L. Andreani, E. Lapi, Bull. Chim. Farm. 99 (1960) 583-586.
[28] D. Tahmasssebi, J.A. Bryson, S.I. Binz, Synth. Commun. 41 (2011) 2701-2711.
[29] D. Azarifar, S. Khatami, R. Nejat-Yami J. Chem. Sci. 126 (2014) 95-101.
[30] A. Rostami, B. Atashkar, H. Gholami, Catal. Commun. 37 (2013) 69-74.
[31] K. Khandan-Barani, M. Kangani, M. Mirbaluchzehi, Z. Siroos, Inorg. Nano-Met. Chem. 47 (2017) 751-755.
[32] S. Gurumurthi, V. Sundari, R. Valliappan, Eur. Chem. Bull. 6 (2017) 211-214.
[33] F. Vendittia, A. Ceglie, G. Palazzo, G. Colafemmina, F. Lopez, J. Colloid Interface Sci. 310 (2007) 353–361.
[34] F. Ahmadi, M.A. Daneshmehr, M. Rahimi, Spectrochim. Acta A 67 (2007) 412–419.
[35] Q. Liu, J. Li, W. Tao, Y. Zhu, S. Yao, Bioelectrochemistry 70 (2007) 301–307.
[36] X-H. Liu, X.-H. Luo, S.-X. Lu, J.-C. Zhang, W.-L.Cao, J. Colloid Interface Sci. 307 (2007) 94–100.
[37] A.C.S. Costa, L.S.G. Teixeira, S.L.C. Ferreira, Talanta 42 (1995) 1973–1978.
[38] S. Yamamoto, S. Kobashi, K.-I. Tsutsui, Y. Sueishi, Spectrochim. Acta A 66 (2007) 302–306.
[39] L.S. de Carvalho, A.C.S. Costa, S.L.C. Ferreira, L.S.G. Teixeira, J. Braz. Chem. Soc. 15 (2004) 153–157.
[40] L.S.G. Teixeira, A.C.S. Costa, S.L.C. Ferreira, M.L. Freitas, M.S. de Carvalho, J. Braz. Chem. Soc. 10 (1999) 519–522.
[41] X. Jain, W. Xuebing, D. Bingyao, High Perform. Polym. 18 (2015) 1-12.
[42] L. Fotouhi, M.M. Heravi, A. Fatehi, K. Bakhtiari, Tetrahedron Lett. 48 (2007) 5379-5381.
[43] S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C.R. Chim. 15 (2012) 394-397.
[44] L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu, J. Fluorine Chem. 127 (2006) 97-100.
[45] R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal Commun. 9 (2008) 307-310.
[46] A. Mobinikhaledi, M.A. Bodaghi Fard, Acta Chim. Slov. 57 (2010) 931-935.
[47] S. Tu, H. Wang, J. Feng, A. Tang, J. Feng, Synth. Commun. 31 (2001) 2663-2666.
[48] N. Hazeri, M.T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35 (2014) 391-395.
[49] V.M. Joshi, R.L. Magar, P.B. Throat, S.U. Tekale, B.R. Patil, M.P. Kale, R.P. Pawar, Chin. Chem. Lett. 25 (2014) 455-458.
[50] S. Banerjee, H. Horn, H. Khatri, G. Sereda, Tetrahedron Lett. 52 (2011) 1878-1881.
[51] S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, P. Salehi, Synth. Commun. 37 (2007) 1097-1108.
[52] S. Gao, C.H. Tsai, C. Tseng, C.F. Yao, Tetrahedron. 64 (2008) 9143-9149.
[53] E. Mosaddegh, A. Hassankhani, G. Mansouri, E-J. Chem. 8 (2011) 529-534.