L-proline: An efficient catalyst for the synthesis of quinoline derivatives in aqueous media
الموضوعات : Iranian Journal of CatalysisElham Davoodi 1 , Leila Youseftabar-Miri 2 , Hamideh Hosseinjani-Pirdehi 3
1 - Chemistry Department, Izeh Branch, Islamic Azad University, Izeh, Iran.
2 - Chemistry Department, Izeh Branch, Islamic Azad University, Izeh, Iran.
3 - Chemistry Department, University of Guilan, 41335-1914, Rasht, Iran.
الکلمات المفتاحية: Multicomponent reactions, Quinoline derivatives, Aqueous media, L-proline,
ملخص المقالة :
An efficient and direct procedure for the synthesis of benzo[h]-indeno[1,2-b]-quinoline derivatives has been described. The procedure employs a three-component condensation reaction in one-pot using 2H-indene-1, 3-dione, naphthalen-1-amine,and aldehydes in the presence of catalytic amount of L-prolinein aqueous media.
[1] (a) N. Mont, J. Teixido, J.I. Borrell, C.O Kappe, Tetrahedron Lett. 44 (2003) 5385-5387. (b) M.C. Bagley, J.W. Dale, J. Bower, Chem. Commun. (2002) 1682-1683. (c) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 24 (2004) 4957-4980. (d) Y.J. Huang, F.Y. Yang, C.J. Zhu. J. Am. Chem. Soc. 127 (2005) 16386-16387.
[2] For selected reviews, see: (a) J. Zhu, H. Bienayme, H. Multicomponent Reactions; Wiley: New York, (2005). (b) S.L. Cui, X.F. Lin, Y.G. Wang. J. Org. Chem. 70 (2005) 2866-2869. (c) C.J. Li, T.H Chan. Organic Reactions in Aqueous Media; Wiley: New York, (1997). (d) P.A. Grieco, Ed.; Thomson Science: Glasgow, Scotland, Organic Synthesis in Water. (1998). (e) C.J. Li. Chem. Rev. 105 (2005) 3095-3166.
[3] (a) R. Breslow, D.C. Rideout, J. Am. Chem. Soc. 102 (1980) 7816-7817. (b) U.M. Lindstrom. Chem. Rev. 102 (2002) 2751-2772. (c) C.I. Herrerias, X. Yao, Z. Li, C.J. Li, Chem. Rev. 107 (2007) 2546-2562.
[4] E.C. Franklin. Chem. Rev. 16 (1935) 305-361.
[5] F.W. Bergstrom. Chem. Rev. 35 (1944) 77-277.
[6] F.W. Lichtenthaler. Acc. Chem. Res. 35 (2002) 728-737.
[7] (a) J.K. Natarajan, J.N. Alumasa, K. Yearick, K.A. Ekoue-Kovi, L.B. Casabianca, A.C. De Dios, C. Wolf, P.D. Rope. J. Med. Chem. 51 (2008) 3466-3479. (b) C. Theeraladanon, M. Arisawa, M. Nakagawa, A. Nisshida,. Tetrahedron: Asymmetry 16 (2006) 827-831.
[8] (a) R. Klingenstein, P. Melnyk, S.R. Leliveld, A. Ryckebusch, C. Korth, J. Med. Chem. 49 (2006) 5300-5308; (b) B. Lal, N.B. Bhise, R.M. Gidwani, A.D. Lakdawala, K. Joshi, S. Parvardhan, ARKIVOC ii (2005) 77-97; (c) P. Benedetti, R. Mannhold, G. Crucianini, Bioorg. Med. Chem. 12 (2004) 3607-3617. (d) T. Staalhandsk, T. Kalland, T. Immunopharmacology 11 (1986) 87-92.
[9] W. Notz, F. Tanaka, C.F. Barbas Acc. Chem. Res. 37 (2004) 580-591. (b) P.I. Dalko, L. Moisan. Angew. Chem. Int. Ed. 43 (2004) 5138-5175.
[10] (a) Y. Wang, Z.C. Shang, T.X. Wu, J. Fan, X.J. Chen. J. Mol. Catal. A: Chem. 253 (2006) 212-218; (b) M. Srinivasan, S. Perumal, S. Selvaraj. Arkivocxi (2005) 201-208; (c) R. Dodda, C.G. Zhao. Synthesis 19 (2006) 3238-3246.
[11] N.G. Kozlov, K.N. Gusak, A.B. Tereshko, S.I. Firgangand, A.S. Shashkov. Org. Khim. 40 (2004) 1228-1233.
[12] N.G. Kozlov, L.I. Basalaevaand L. Yu. Zh. Org. Khim. 38 (2002) 1218-1222.
[13] N.G. Kozlov, K.N. Gusak. Russ. J. Org. Chem. 42 (2006) 1668−1674.
[14] X.S. Wang. M.M. Zhang, Z.S. Zeng. J. Heterocyclic Chem. 43 (2006) 989-995.
