β-Cyclodextrin conjugated imidazolium cation: A neutral, eco-friendly and water-miscible dicationic ionic liquid in the regioselective ring opening of epoxides
محورهای موضوعی : Iranian Journal of CatalysisFatemeh Moheiseni 1 , Ali Reza Kiasat 2
1 - Department of Chemistry, Islamic Azad University, Ahvaz Branch, Ahvaz, Iran.
2 - Department of Chemistry, College of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran.
کلید واژه: Dicationic ionic liquid, β-Cyclodextrin conjugated imidazolium cation, Regioselective ring opening of the epoxides, β-azidoalcohols, β-cyanohydrins, β-thiocyanohydrins,
چکیده مقاله :
The present study, for the first time, presents a feasible protocol for the preparation of β-cyclodextrin/ imidazolium based dicationic ionic liquid, [βCD/Im](OTs)2, and its application as an efficient and eco-friendly microvessel and host ionic liquid system for the regioselective ring opening of the epoxides in water. No evidence for the formation of diol by-products or side reactions, such as isomerization, epimerization and rearrangements was observed and 1,2-disubstituted products, β-azidoalcohols, β-cyanohydrins, and β-thiocyanohydrins, obtained in pure form. Short reaction time, easy reaction conditions, simple work-up procedure, high yield, reusability, and use of an eco-friendly catalyst are some of the striking features of the present protocol.
[1] T. Ollevier, G. Lavie-Compin, Tetrahedron Lett. 45 (2004) 49-52.
[2] A.R. Kiasat, S. Nazari, J. Davarpanah, C. R. Chim. 17 (2014) 124-130.
[3] B. Tamami, H. Mahdavi, Tetrahedron Lett. 42 (2001) 8721-8724.
[4] N. Iranpoor, H. Firouzabadi, M. Shekarize, Org. Biolmol. Chem. 1 (2003)724-727.
[5] A. R. Kiasat, F. Ataeian, M. Falah-Mehrjardi., Iran. J. Catal. 2 (2012) 1-9.
[6] F. Kazemi, A.R. Kiasat, S. Ebrahimi, Synth. Commun. 33 (2003) 999-1004.
[7] (a) A.R. Kiasat, R. Badri, B. Zargar, S. Sayyahi, J. Org. Chem. 73 (2008) 8382-8385, (b) A.R. Kiasat, M. Zayadi, Catal. Commun. 9 (2008) 2063-2067, (c) A.R. Kiasat, M. Fallah-Mehrjardi, J. Iran. Chem. Soc. 6 (2009) 542-546, (d) A. R. Kiasat, R. Mirzajani, H. Shalbaf, M. Fallah-Mehrjardi, J. Chin. Chem. Soc. 56 (2009) 594-599, (e) A. Mouradzadegun, A.R. Kiasat, P. Kazemian Fard, Catal. Commun. 29 (2012) 1-5, (f) A.R. Kiasat, F. Chadorian, S. J. Saghanezhad, C. R. Chim. 18 (2015) 1297-1306, (g) S. Yousefi, A.R. Kiasat, RSC Adv. 5 (2015) 92387-92393.
[8] (a) M. Chini, P. Crotti, F. Macchia, Tetrahedron Lett. 31 (1999) 5641-5644, (b) B. Yadollahi, H. Danafar, Catal. Lett. 113 (2007) 120-123.
[9] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, M. Norouzi, M. Moein, Res. Chem. Intermed. 41 (2015) 8665-8672.
[10] Paradowska, M. Stodulski, J. Mlynarski, Angew. Chem. 121 (2009) 4352-4362.
[11] D. Kogelniga, A. Stojanovica, F. Kammerb, P. Terzieffc, M. Galanskia, F. Jirsaa, R. Krachlera, T. Hofmannb, B.K. Kepplera, Inorg. Chem. Commun. 13 (2010) 1485-1488.
[12] S.T. Handy, X.L. Zhang, Org. Lett. 3 (2001) 233-236.
[13] P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 39 (2000) 3772-3789.
[14] P. Wasserscheid, R. van Hal, A. Bosmann, Green Chem. 4 (2002) 400-404.
[15] Youming, Z., Xinrong, D., Liangcheng, W., Taibao, W. J. Incl. Phenom. Macrocycl. Chem. 60 (2008) 313-319.
[16] H. Chen, H. Ji, X. Zhou, L, Wang, Tetrahedron. 66 (2010) 9888-9893.
[17] G.K.E.V. Scriba, J. Sep. Sci. 31 (2008) 1991-2011.
[18] K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 98 (1998) 2045-2076.
[19] E.Y. Ozmen, M. Sezgin, A. Yilmaz, M. Yilmaz, Bioresour. Technol. 99 (2008) 526-531.
[20] R.Villalonga, R. Cao, A. Fragoso, Chem. Rev. 107 (2007) 3088-3116.
[21] G. Tripodo, C. Wischke, A.T. Neffe, A. Lendlein, Carbohydr. Res. 381 (2013) 59-63.
[22] J.F. Ma, J.F. Lio, Y. Xing, H.Q. Jia, Y.H. Lin, J. Soc. Dalton Trans. 14 (2000) 2403-2407.
[23] H. Sharghi, A. Hasani Nejad, M.A. Nasseri, New. J. Chem. 28 (2004) 946-951.
[24] A.R. Khan, P. Forgo, K.J. Stine, V.T. D’Souza, Chem. Rev. 98 (1998) 1977-1996.
[25] X.M. Gao, L.H. Tong, Y. Inoue, A. Tai, Synth. Commun. 25 (1995) 703-710.