Eco-Friendly and One-Pot Synthesis of 1,8-Dioxooctahydroxanthene Derivatives Catalyzed by Task-Specific Brønsted Acidic Ionic Liquid
محورهای موضوعی : Iranian Journal of Catalysis
Hossein Naeimi
1
,
Zahra Sadat Nazifi
2
1 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, Iran.
2 - Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, Iran.
کلید واژه: 1, Ionic Liquid, Dimedone, Catalyst, Aromatic aldehydes, 8‐Dioxooctahydroxanthenes,
چکیده مقاله :
Efficient and one-pot synthesis of 1,8-dioxo-octahydroxanthenes was described by Knoevenagel condensation, Michael addition and cyclodehydration of dimedone. This reaction was carried out through condensation of dimedone and various aromatic aldehydes in the presence of task-specific Brønsted acidic ionic liquid under solvent free conditions. The catalyst could be recycled five times without significant loss of its catalytic activity.
[1] T. Welton, Chem. Rev. 99 (1999) 2071-2084.
[2] X. Tong, Y. Li, Chem. Sus. Chem. 3 (2010) 350-355.
[3] R.A. Sheldon, R. Maderia-Lau, M.J. Sorgedrager, F.V. Rantwijk, K.R. Seddon, Green Chem. 4 (2002) 147-151.
[4] A. Visser, R.P. Swatloski, R.D. Rogers, Green Chem. 2 (2000) 1-4.
[5] A. Bosmann, L. Datsevich, A. Jess, A. Lauter, C. Schmitz, P. Wassercheid, Chem. Commun. 23 (2001) 2494-2495.
[6] Z.M. Liu, Z.Y. Sun, B.X. Han, J.L. Zhang, J. Huang, J.M. Du, S.D. Miao, J. Nanosci. Nanotech. l6 (2006) 175-179.
[7] H. Pinkowska, Polymer 51 (2006) 836-842.
[8] B.M. Quinn, Z. Ding, R. Moulton, A.J. Bard, Langmuir 18 (2002) 1734-1742.
[9] M.P. Rafael, J. Mex. Chem. Soc. 51 (2007) 252-264.
[10] B. Søballe, K.P. Robert, Microbiology 145 (1999) 1817-1830.
[11] K. Muharrem, B. Erhan, C. Ferdag, Med. Chem. Res. 20 (2011) 1214-1219.
[12] J. Amitabh, B. Jennifer, Tetrahedron Lett. 45 (2004) 8999-9001.
[13] W. Su, D. Yang, C. Jin, B. Zhang, Tetrahedron Lett. 49 (2008) 3391-3394.
[14] R.M. Ion, D. Frackowiak, A. Planner, K. Wiktorowicz, Acta Biochim. Pol. 45 (1998) 833-844.
[15] S. Sudha, M.A. Pasha, Ultrason. Sonochem. 19 (2012) 994-998.
[16] M. Ahmad, T.A. King, D. Ko, B.H. Cha, J. Lee, J. Phys. D-Appl. Phys. 35 (2002) 1473-1476.
[17] C.G. Knight, T. Stephens, Biochem. J. 258 (1989) 683-689.
[18] H.R. Shaterian, A. Hosseinian, M. Hashang, Turk. J. Chem. 33 (2009) 233-240.
[19] H. Zang, Y. Zhang, B. Cheng, W. Zhang, X. Xu, Y. Ren, Chin. J. Chem. 30 (2012) 362-366.
[20] I. Mohammadpoor-Baltork, M. Moghadam, V. Mirkhani, S. Tangestaninejad, H.R. Tavakoli, Chin. Chem. Lett. 22 (2011) 9-12.
[21] K. Venkatesan, S.S. Pujari, R.J. Lahoti, K.V. Srinivasan, Ultrason. Sonochem. 15 (2008) 548-553.
[22] A. Rahmati, Chin. Chem. Lett. 21 (2010) 761-764.
[23] A.N. Dadhania, V.K. Patel, D.K. Raval, C. R. Chim. 15 (2012) 378-383.
[24] A. Ilangovan, S. Malayappasamy, S. Muralidharan, M. Sundaram, Chem. Cent. J. 5 (2011) 81-86.
[25] H. Naeimi, Z.S. Nazifi, J. Ind. Eng. Chem. 20 (2014) 1043–1049.
[26] R.J. Kalbasi, A.R. Massah, B. Daneshvarnejad, Appl. Clay Sci. 55 (2012) 1-9.
[27] K.V. Girijesh, R. Keshav, K.V. Rajiv, D. Pratibha, M.S. Singh, Tetrahedron 67 (2011) 3698-3706.
[28] A.K. Zarea, M. Mokhlesi, A.R. Hasaninejad, T. Hekmat-Zadeh, E-J. Chem. 9 (2012) 1854-1863.
[29] G.H. Mahdavinia, M.A. Bigdeli, Y. Saeidi Hayeniaz, Chin. Chem. Lett. 20 (2009) 539-541.
[30] S. Kantevari, R. Bantu, L. Nagarapu, J. Mol. Cat. A: Bhem. 269 (2007) 53-57.
[31] K. Swapna, M.S. Narayana, D.N.Y. Venkata, Eur. J. Chem. 2 (2011) 272-275.
