Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for cyclization of 2- aminochalcones to 2- aryl-2,3- dihydroquinolin- 4(1H)- ones

Iranian Journal of Catalysis

مقاله 3، دوره 4، شماره 4، اسفند 2014، صفحه 235-239   

نوع مقاله: Articles

نویسندگان

Hossein Eshghi^* ؛ Mohammad Rahimizadeh؛ Seyed Mohsen Mousavi

Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran.

چکیده

Silica ferric hydrogensulfate is an efficient heterogeneous catalyst for the cyclization of 2- aminochalcones to the corresponding 2,3-dihydroquinolin- 4(1H)-ones. This intramolecular aza Michael reaction was carried out in high yields using chalcones bearing of electron donating and electron withdrawing groups. The catalyst is reusable without significant decreases in its activity after four times recycling.The present study represents the application of silica supported ferric hydrogensulfate as catalyst for the aza-Michael cyclization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolone derivatives. Therefore, the simplicity of the procedure, the mildness of the reaction conditions, high yields, the ease of catalyst separation and its re-usability demonstrates the ability of this method.

کلیدواژه‌ها

Fe(HSO4)3؛ Heterogeneous؛ Dihydroquinolone- 4(1H)- ones؛ Chalcones؛ aza- Michael

مراجع

[1] R. Pingaew, A. Saekee, P. Mandi, C. Nantasenamat, S. Prachayasittikul, S. Ruchirawat, V. Prachayasittikul, Europ. J. Med. Chem. 85 (2014) 65-76.
[2] A. Pejović, I. Damljanović, D. Stevanović, M. Vukićević, S.B. Novaković, G.A. Bogdanović, N. Radulović, R.D. Vukićević, Polyhedron 31 (2012) 789-795.
[3] A.L. Tokes, G. Litkei, Synth. Commun. 23 (1993) 895-902.
[4] N. Ahmed, J.E. van Lier, Tetrahedron Lett. 48 (2007) 13-15.
[5] R. Abonia, P. Cuervo, J. Castillo, B. Insuasty, J. Quiroga, M. Nogueras, J. Cobo, Tetrahedron Lett. 49 (2008) 5028-5031.
[6] N. Ahmed, J.E. van Lier, Tetrahedron Lett. 47 (2006) 2725-2729.
[7] M. Chelghoum, M. Bahnous, A. Bouraiou, S. Bouacida, A. Belfaitah, Tetrahedron Lett. 53 (2012) 4059-4061.
[8] D. Kumar, G. Patel, B.G. Mishra, R.S. Varma, Tetrahedron Lett. 49 (2008) 6974-6976.
[9] R. Sakirolla, M. Yaeghoobi, N.A. Rahman, Monatsh. Chem. 143 (2012) 797-800.
[10] K.C. Lekhok, D. Bhuyan, D. Prajapati, R.C. Boruah, Mol. Div. 14 (2010) 841-846.
[11] P. Kumar, D.N. Dhar, Synth. Commun. 25 (1995) 1933-1938.
[12] N. Ahmed, H. Kumar, B.V. Babu, Synth. Commun. 43 (2013) 567-581.
[13] R.N. Bhattacharya, P. Kundu, G. Maiti, Synth. Commun. 40 (2010) 476-481.
[14] V.K. Rao, M.S. Rao, A. Kumar, J. Het. Chem. 48 (2011) 1356-1360.
[15] H. Eshghi, M. Bakavoli, H. Moradi, Org. Prep. Proced. Int. 43 (2011) 302-307.
[16] H. Eshghi, S.M. Seyedi, E. Safaei, M. Vakili, A. Farhadipour, M. Bayat-Mokhtari, J. Mol. Cat. A: Chem. 363–364 (2012) 430-436.
[17] H. Eshghi, M. Rahimizadeh, M. Hosseini, A. Javadian-Saraf, Monatsh. Chem. 144 (2012) 197-203.
[18] H. Eshghi, M. Rahimizadeh, N. Attaran, M. Bakavoli, J. Iran. Chem. Soc. 10 (2013) 1151-1157.
[19] A. Khojastehnezhad, M. Rahimizadeh, H. Eshghi, F. Moeinpour, Chin. J. Cat. 35 (2014) 376-382.
[20] H. Eshghi, M. Rahimizadeh, S. Saberi, Catal. Commun. 9 (2008) 2460-2466.
[21] Y.M. Lin, Y. Zhou, M.T. Flavin, L.M. Zhou, W. Nie, F.C. Chen, Bioorg. Med. Chem. 10 (2002) 2795-2802.
[22] R.A. Bunce, B. Nammalwar, J. Het. Chem. 48 (2011) 613-619.
[23] U.P. Lad, M.A. Kulkarni, U.V. Desai, P.P. Wadgaonkar, C.R. Chim. 14 (2011) 1059-1064.
[24] L. Jianjun, J. Linyong, Y. Chuanming, S. Weike. J. Chem. Res. 33 (2009) 170-173.
[25] D. Kumar, G. Patel, A. Kumar, J. Het. Chem. 46 (2009) 791-795.
[26] H. Eshghi, M. Rahimizadeh, S.M. Mousavi, Nat. Prod. Res. 28 (2014) 438-443.