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

الموضوعات : Iranian Journal of Catalysis

Mohammad Ebrahim Sedaghat ¹ (Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, Iran.)
Faranak Farhadi ² (Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, Iran.)
Mohammad Reza Nazarifar ³ (Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, Iran.)
Rezvan Sheikhi Kamareji ⁴ (Department of Chemistry, Lamerd Branch, Islamic Azad University, Lamerd, Iran.)

تاريخ الإرسال : 19 الخميس , رجب, 1439 تاريخ التأكيد : 20 الأحد , محرم, 1440 تاريخ الإصدار : 23 السبت , ربيع الأول, 1440

الکلمات المفتاحية: green chemistry, Multi-component reactions, One-pot synthesis, Hydrophobic-bentonite, Pyran derivatives,

ملخص المقالة :

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.

المصادر:

[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.