Chinese Journal of Organic Chemistry >
CuBr2-Catalyzed Three-Component Coupling for Synthesis of Quinoline-2,4-dicarboxyl Derivatives
Received date: 2014-01-13
Revised date: 2014-03-12
Online published: 2014-04-15
Supported by
Project supported by the Applied Basic Research Plan of Yunnan Province Science and Technology Department (No. 2011FZ097).
A convenient and efficient method for synthesizing quinoline-2,4-dicarboxyl derivatives has been developed via a simple one-pot reaction of aromatic amines, glyoxylic ester, and pyruvate using low-costing CuBr2 as a catalyst. The method is atom efficiency, and utilizes non-expensive catalysts and easily available reagents, which provides an attractive approach to quinoline-2,4-dicarboxyl derivatives. This process has potential applications in the synthesis of biologically and medicinally relevant compounds.
Wang Kou , Yu Haofei , Ding Linfen , Hu Jianlin . CuBr2-Catalyzed Three-Component Coupling for Synthesis of Quinoline-2,4-dicarboxyl Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1437 -1441 . DOI: 10.6023/cjoc201401020
[1] Bilker, O.; Lindo, V.; Panico, M.; Etienne, A. E.; Paxton, T.; Dell, A.; Rogers, M.; Sinden, R. E.; Morris, H. R. Nature 1998, 392, 289.
[2] Hazeldine, S. T.; Polin, L.; Kushner, J.; White, K.; Corbett, T. H.; Horwitz, J. P. Bioorg. Med. Chem. 2006, 14, 2462.
[3] (a) Luo, W.; Zhang, Z.; Wang, C. J. Chin. J. Org. Chem. 2013, 33, 125 (in Chinese).
(罗稳, 张震, 王超杰, 有机化学, 2013, 33, 125.)
(b) Cappelli, A.; Mohr, G. P.; Gallelli, A.; Rizzo, M.; Anzini, M.; Vomero, S.; Mennuni, L.; Ferrari, F.; Makovec, F.; Menziani, M. C.; Benedetti, P. G. D.; Giorgi, G. J. Med. Chem. 2004, 47, 2574.
[4] (a) Gross, D. J.; Weiss, L.; Reibstein, I.; Hedlund, G.; Dahlen, E.; Rapoport, M. J.; Slavin, S. Int. Immunopharcol. 2001, 1, 1131.
(b) Dahlen, E.; Dawe, K.; Ohlsson, L.; Hall, H.; Hedse, K.; Annersten, K.; Astrom, M.; Gross, D. J.; Hedlund, G. Int. Immunopharcol. 2003, 3, 17.
[5] Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021.
[6] (a) Carrigan, C. N.; Bartlett, R. D.; Esslinger, C. S.; Cybulski, K. A.; Tongcharoensirikul, P.; Bridges, R. J.; Thompson, C. M. J. Med. Chem. 2002, 45, 2260.
(b) Carrigan, C. N.; Esslinger, C. S; Bartlett, R. D.; Bridges, R. J.; Thompson, C. M. Bioorg. Med. Chem. Lett. 1999, 9, 2607.
[7] Laras, Y.; Hugues, V.; Chandrasekaran, Y.; Blanchard-Desce, M.; Acher, F. C.; Pietrancosta, N. J. Org. Chem. 2012, 77, 8294.
[8] (a) Carling, R. W.; Leeson, P. D.; Moseley, A. M.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R. J. Med. Chem. 1992, 35, 1942.
(b) Rice, K. C.; Boone, B. J.; Rubin, A. B.; Rauls, T. J. J. Med. Chem. 1976, 19, 887.
[9] (a) Zhu, H.; Yang, R. F.; Yun, L. H.; Li, J. Chin. Chem. Lett. 2010, 21, 35.
(b) Rineh, A.; Khalilzadeh, M. A.; Hashemi, M. M.; Rajabi, M.; Karimi, F. J. Heterocycl. Chem. 2012, 49, 789.
(c) Wei, W.; Wen, J. W.; Yang, D. S.; Sun, X. J.; You, J. M.; Suo, Y. R.; Wang, H. Tetrahedron 2013, 69, 10747.
(d) Doebner, O.; Miller, W. V. Berichte 1883, 16, 24.
(e) Li, J. J. Name Reactions in Heterocyclic Chemistry, John Wiley & Sons, Inc., Hoboken, New Jersey, 2005, p. 407.
(f) Itoh, S.; Fukui, Y.; Haranou, S.; Ogino, M.; Komatsu, M.; Ohshiro, Y. J. Org. Chem. 1992, 57, 4452.
(g) Carling, R. W.; Leeson, P. D.; Moseley, A. M.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R. J. Med. Chem. 1992, 35, 1942.
(h) Itoh, S.; Kato, J.; Inoue, T.; Kitamura, Y.; Komatsu, M.; Ohshiro, Y. Synthesis 1987, 1067.
[10] (a) Nakajima, T.; Inada, T.; Igarashi, T.; Sekioka, T.; Shimizu, I. Bull. Chem. Soc. Jpn. 2006, 79, 1941.
(b) Inada, T.; Nakajima, T.; Shimizu, I. Heterocycles 2005, 66, 611.
/
| 〈 |
|
〉 |
