Sulfonated Porous Carbon (SPC): An efficient and recyclable solid acid catalyst for one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions
الموضوعات : Iranian Journal of CatalysisArash Shokrolahi 1 , Abbas Zali 2 , Mohammad Ali Zarei 3 , Karim Esmaeilpour 4
1 - Chemistry Department, Malek-ashtar University of Technology, Shahin-shahr, P.O.Box 83145-115, I. R. Iran.
2 - Chemistry Department, Malek-ashtar University of Technology, Shahin-shahr, P.O.Box 83145-115, I. R. Iran.
3 - Chemistry Department Faculty of Materials, Malek-ashtar University of Technology, Tehran, I.R. Iran.
4 - Chemistry Department, Malek-ashtar University of Technology, Shahin-shahr, P.O.Box 83145-115, I. R. Iran.
الکلمات المفتاحية: Solid acid, Heterogeneous catalysis, Sulfonated Porous Carbon, 2, 3 dihydroquinazolin-4(1H)-ones,
ملخص المقالة :
A simple and efficient procedure has been developed for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones derivatives under solvent-free conditions. This method uses the condensation of isatoic anhydride, aldehydes, and amines in the presence of a catalytic amount Sulfonated Porous Carbon (SPC). One of the important advantages of the new method is that the SPC could be recycled and reused.
[1] J.B. Jiang, D.P. Hesson, B.A. Dusak, D.L. Dexter, G.L. Kang, E. Hamel, J. Med. Chem. 33 (1990) 1721-1728.
[2] A.M. Farghaly, R. Soliman, M.A. Khalil, A.A. Bekhit, A.E. A. Bekhit, Boll. Chim. Farm. 141 (2002) 372-378.
[3] J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell, T.D. Greenwood ,J. Med. Chem. 33(1990) 161-166.
[4] Y. Kurogi, Y. Inoue, K. Tsutsumi, S. Nakamura, K. Nagao, H. Yoshitsugu, Y. Tsuda, J. Med .Chem. 39(1996) 1433-1437.
[5] M. Hour, L. Huang, S. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K. Lee, J. Med. Chem. 43(2000) 4479-4487.
[6] Y.H. Na, S.H. Hong, J.H. Lee, W.K. Park, D.J. Baek, H.Y. Koh, Y.S. Cho, H. Choo, A.N. Pae, Bioorg. Med. Chem. 16 (2008) 2570-2578.
[7] J.M. Khurana, G. Kukreja, J. Heterocycl. Chem. 40 (2003) 677-679.
[8] W. Su, B. Yang, Aust. J. Chem. 55(2002) 695-697.
[9] D. Shi, L. Rong, J. Wang, Q. Zhuang, X. Wang, H. Hu, Tetrahedron Lett. 44 (2003) 3199-3201.
[10] S.D. Sharma, V. Kaur, Synthesis. (1989) 677-680.
[11] P.T. Anastas, J. C. Warner, Green Chemistry, Theory and Practice, Oxford University Press, London, 1998.
[12] J. H. Clark, Green .Chem. 1(1999) 1-8.
[13] H. Firouzabadi, A. A. Jafari, J. Iran. Chem. Soc., 2 (2005) 85-114.
[14] R.A. Sheldon, H. Van Bekkum (Eds.), Catalysis Through Heterogeneous Catalysis, Wiley/VCH, Weinheim, Germany, 2002.
[15] J.H. Clark, Acc. Chem. Res. 35 (2002) 791-797.
[16] A. Corma, Chem. Rev. 95 (1995) 559-624.
[17] M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, M. Hosseini, Tetrahedron Lett. 44 (2003) 4579–4580.
[18] V.A. Likholobov, V.F. Surovikin, G.V. Plaksin, M.S. Tsekhanovich, Yu. V. Surovikin, O.N. Baklanova, Catal. Ind. 1 (2009) 11–16.
[19] S.M. Manocha, Sādhanā 28 (2003) 335–348.
[20] M.O. Marı́n, C.F. González, A.M. Garcı́a, V.G. Serrano, Appl. Surf. Sci. 252 (2006) 5967-5971.
[21] M. Kitano, K. Arai, A. Kodama, T. Kousaka, K. Nakajima, S. Hayashi, M. Hara. Catal. Lett, 131 (2009) 242-249.
[22] (a) M. Hudlicky, Oxidations in Organic Chemistry, ACS Monograph Ser. 186, American Chemical Society, Washington, D.C. 1990. (b) B.M. Trost, Fleming I. Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1st Ed, vol. 7, 1991.
[23] M. Kochi,. Green Reaction Media for Organic Synthesis. Blackwell: Oxford, 2005.
[24] K.R. Seddon, Nature. (London) 2 (2003) 363-374.
[25] J.B. Lee, Y.K. Park, O.B. Yang, Y. Kanga, K. Jun, Y.J. Lee, H.Y. Kima, K.H. Lee, W.C. Choi, J. Power. Sources 158 (2006) 1251-1255.
[26] P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth. Commun. 36(2006) 2287-2292.
[27] M. Dabiri, P. Salehi, M. Baghbanzadeh, M.A. Zolfigol, M. Agheb, S. Heydari Catal Commun. 9 (2008) 785-788.
[28] M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgarya, A.A. Mohammadi Tetrahedron Lett. 46 (2005) 6123-6126.
[29] L.M. Wang, L. Hu, J.H. Shao, T. Yu, L. Zhang J. Fluorine Chem. 129 (2008) 1139-1145.
[30] A. Saffar-Teluri, S. Bolouk, Monatsh. Chem. 141 (2010) 1113-1115.
[31] J.X. Chen, D. Wu, F. He, M.C. Liu, H. Wu, J.C. Ding, W.K. Su, Tetrahedron Lett. 49 (2008) 3814-3818.
[32] Z. Karimi-Jaberi, R. Arjmandi, Monatsh. Chem. 142 (2011) 631–635.
