Snail shell as a natural and highly efficient catalyst for the synthesis of imidazole derivatives
الموضوعات : Iranian Journal of CatalysisZakaria Benzekribe 1 , Houda Serrar 2 , Abdelkebir Zarguil 3 , Said Boukhris 4 , Abdelaziz Souizi 5
1 - Laboratory of Organic Chemistry, Organometallic and Theoretical. Faculty of Sciences, Ibn Tofaïl University, BO 133, 14000 Kenitra, Morocco.
2 - Laboratory of Organic Chemistry, Organometallic and Theoretical. Faculty of Sciences, Ibn Tofaïl University, BO 133, 14000 Kenitra, Morocco.
3 - Laboratory of Organic Chemistry, Organometallic and Theoretical. Faculty of Sciences, Ibn Tofaïl University, BO 133, 14000 Kenitra, Morocco.
4 - Laboratory of Organic Chemistry, Organometallic and Theoretical. Faculty of Sciences, Ibn Tofaïl University, BO 133, 14000 Kenitra, Morocco.
5 - Laboratory of Organic Chemistry, Organometallic and Theoretical. Faculty of Sciences, Ibn Tofaïl University, BO 133, 14000 Kenitra, Morocco.
الکلمات المفتاحية: Heterogeneous catalysis, Green catalysts, Snail shell, 1, 5-tetraaryl-1H-imidazole, 2, 4, 5-triaryl-1H-imidazole,
ملخص المقالة :
A convenient, simple and green process for the synthesis of 2,4,5-triaryl-1H-imidazole and 1,2,4,5-tetraaryl-1H-imidazole derivatives using snail shell, which is abundant in Morocco, as a catalyst in ethanol at 40 °C has been developed. Additionally, short reaction times, excellent yields, simple procedure and relative non-toxicity of the catalyst are other noteworthy advantages and make this method an interesting alternative to other methodologies. Finally, this solid catalyst can be recovered and reused at least seven times with negligible loss in activity. The catalyst has been characterized by X-ray diffraction, scanning electron microscope, Fourier transforms infrared spectroscopy (FT-IR) and measuring the specific surface.
[1] B.L. Vallee, D.S. Auld, Biochemistry 29 (1990) 5647-5659.
[2] S.K. Thompson, K.H.M. Murthy, B. Zhao, E. Winborne, D.W. Green, S.M. Fisher, R.L. Desjarlais, T.A. Tomaszek, T.D. Meek, J. Med. Chem. 37 (1994) 3100-3107.
[3] H. Sensui, M. Gonda, T. Ohara, Jpn. Kokai Tokkyo Koho (1987) JP 6294841.
[4] T. Maier, R. Schmierer, K. Bauer, H. Bieringer, H. Buerstell, B. Sachse, US Patent (1989) 4820335.
[5] S.E. Wolkenberg, D.D. Wisnosak, W.H. Leister, Y. Wang, Z. Zhao, C.W. Lindsley, Org. Lett. 6 (2004) 1453-1456.
[6] A.F. Pozherskii, A.T. Soldatenkov, A.R. Katritzky, Heterocycles in Life Society, Wiley, New York, 2011.
[7] J.G. Lombardino, E.H. Wiseman, J. Med. Chem. 17 (1974) 1182-1188.
[8] J.W. Blank, G.J. Durant, J.C. Emmett, C.R. Ganellin, Nature 248 (1974) 65-67.
[9] B.A. Omotowa, J.M. Shreeve, Organometallics 23 (2004) 783-791.
[10] P. Koch, C. Bäuerlein, H. Jank, S. Laufer, J. Med. Chem. 51 (2008) 5630-5640.
[11] J.C. Lee, J.T. Laydon, P.C. McDonnell, T.F. Gallagher, S. Kumar, D. Green, D. McNulty, M.J. Blumenthal, J.R. Keys, S.W.L. Vatter, J.E. Strickler, M.M. McLaughlin, I.R. Siemens, S.M. Fisher, G.P. Livi, J.R. White, J.L. Adams, P.R. Young, Nature 372 (1994) 739-746.
[12] A.K. Takle, M.J. Brown, S. Davies, D.K. Dean, G. Francis, A. Gaiba, A.W. Hird, F.D. King, P.J. Lovell, A. Naylor, A.D. Reith, J.G. Steadman, D.M. Wilson, Bioorg. Med. Chem. Lett. 16 (2006) 378-381.
[13] (a) A.Y. Usyatinsky, Y.L. Khmelnitsky, Tetrahedron Lett. 41 (2000) 5031-5034. (b) H.A. Oskooie, Z. Alimohammadi, M.M. Heravi, Heteroat. Chem. 17 (2006) 699-702.
[14] (a) S.A. Siddiqui, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron 61 (2005) 3539-3546. (b) H. Zang, Q. Su, Y. Mo, B.-W. Cheng, S. Jun, Ultrason. Sonochem. 17 (2010) 749-751.
[15] C. Yu, M. Lei, W. Su, Y. Xie, Synth. Commun. 37 (2007) 3301-3309.
[16] N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Synthesis 18 (2007) 2829-2834.
[17] M.V. Chary, N.C. Keerthysri, S.V. Vupallapati, N. Lingaiah, S. Kantevari, Catal. Commun. 9 (2008) 2013-2017.
[18] J.N. Sangshetti, N.D. Kokare, S.A. Kotharkara, D.B. Shinde, J. Chem. Sci. 120 (2008) 463-467.
[19] J. Wang, R. Mason, D. VanDerveer, K. Feng, X.R. Bu, J. Org. Chem. 68 (2003) 5415-5418.
[20] A. Shaabani, A. Rahmati, J. Mol. Catal. A: Chem. 249 (2006) 246-248.
[21] K. Niknam, M.R. Mohammadizadeh, S. Mirzaee, D. Saberi, Chin. J. Chem. 28 (2010) 663-669.
[22] M.M. Heravi, M. Zakeri, N. Karimi, M. Saeedi, H.A. Oskooie, N. Tavakoli-Hosieni, Synth. Commun. 40 (2010) 1998-2006.
[23] J. Safari, S.D. Khalili, S.H. Banitaba, J. Chem. Sci. 122 (2010) 437-441.
[24] S.V. Nalage, M.B. Kalyankar, V.S. Patil, S.V. Bhosale, S.U. Deshmukh, R.P. Pawar, Open Catal. J. 3 (2010) 58-61.
[25] J. Safari, S.D. Khalili, M. Rezaei, S.H. Banitaba, F. Meshkani, Monatsh. Chem. 141 (2010) 1339-1345.
[26] K. Sivakumar, A. Kathirvel, A. Lalitha, Tetrahedron Lett. 51 (2010) 3018-3021.
[27] E.O. Jatto, I.O. Asia, E.E. Egbon, J.O. Otutu, M.E. Chukwuedo, C.J. Ewansiha Academia Arena 2 (2010) 32-36.
[28] G.S. Kumar, L.Sathish, R. Govindan, E.K.Girija., RSC Adv. 5 (2015) 39544-39548.
[29] a) M. Ren, C. Dong, C. An, Materials 4 (2011) 1375-1383. b) Z. Hu, Y. Deng, Powder Technol. 140 (2004) 10-16. c) K.N. Islam, M.E. Ali, M.Z.B.A. Bakar, M.Y. Loqman, A. Islam, M.S. Islam, M.M. Rahman, A. Ullah, Powder Technol. 246 (2013) 434-440. d) J. Chen, L. Xiang, Powder Technol. 189 (2009) 64-69. e) H.Y. Ma, I.S. Lee, Mater. Sci. Eng. C 26 (2006) 721-723.
[30] H. Essabir, M.O. Bensalah, D. Rodrigue, R. Bouhfid, A.E. Qaiss, Constr. Build. Mater. 134 (2017) 549-555.
[31] A. Teimouri, A. N. Chermahini, J. Mol. Catal. A: Chem. 346 (2011) 39-45.
[32] A. Shaabani, A. Rahmati, E. Farhangi, Z. Badri, Catal. Commun. 8 (2007) 1149-1152.
[33] B. F. Mirjalili, A. Bamoniri, M.A. Mirhoseini, Scientia Iranica 20 (2013) 587-591.
[34] A. Khazaei, H.A.A. Nik, A. Ranjbaran, A.R. Moosavi-Zare, RSC Adv. 6 (2016) 78881-78886.
[35] J. Safari, S. Naseh, Z. Zarnegar, Z Akbari, J. Taibah. Univ. Sci. 8 (2014) 323-330.
[36] S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65 (2009) 10155-10161.
[37] F. Nemati, A. Elhampour, M.B. Natanzi, Inorg. Nano-Met. Chem. 47 (2017) 666-671.
[38] D. Wang, Z. Li, X. Huang, Y. Li, ChemistrySelect. 4 (2016) 664-668.
[39] S.U. Bhat, R.A. Naikoo, R. Tomar, Int. Res. J. Pure Appl. Chem. 11 (2016) 1-10.
[40] R. Mirsafaei, M.M. Heravi, S. Ahmadi, T. Hosseinnejad, Chem. Pap. 70 (2016) 418-429.
[41] A. Olyaei, Z. Derikvand, F. Noruzian, M. Sadeghpour, Iran. Chem. Commun. 4 (2016) 337-346.
[42] H. Sharghi, M. Aberi, M.M. Doroodmand, Molec. Divers 19 (2015) 77-85.
[43] M. Bakavoli, H. Eshghi, A. Mohammadi, H. Moradi, J. Ebrahimi, Iran. J. Catal. 5 (2015) 237-243.
[44] M. Esmaeilpour, J. Javidi, M. Zandi, New J. Chem. 39 (2015) 3388-3398.
[45] A. Ghorbani-Choghamarani, M. Hajjami, F. Gholamian, G. Azadi, Russ. J. Org. Chem. 51 (2015) 352-356.
[46] A. Ghorbani-Choghamarani, F. Ghorbani, Z. Yousofvand, G. Azadi, J. Porous Mater. 22 (2015) 665-673.
[47] B. Sadeghi, B.B.F. Mirjalili, M.M. Hashemi, Tetrahedron Lett. 49 (2008) 2575-2577.
[48] K. Niknam, A. Deris, F. Naeimi, F. Majleci, Tetrahedron Lett. 52 (2011) 4642-4645.
[49] N. Iravani, N.S. Mohammadzade, K. Niknam, Chin. Chem. Lett. 22 (2011) 1151-1154.
[50] G. Ahmadi-Ana, S. Mohammad, M. Baghernejad, K. Niknam, Chin. J. Chem. 30 (2012) 517-521.
[51] Z. Tavakoli, M. Bagherneghad, K. Niknam, J. Heterocycl. Chem. 49 (2012) 634-639.
