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http://dx.doi.org/10.5012/jkcs.2012.56.3.322

New Efficient Synthesis of 3-Carboxylquinolines  

Kirankumar, S. (Department of Chemistry, K L University)
Rambabu, D. (Department of Chemistry, K L University)
Sekhar, N. Chandra (Department of chemistry, Krishna University)
Prasad, A.S.G. (Department of chemistry, Krishna University)
Rao, M.V. Basaveswara (Department of chemistry, Krishna University)
Publication Information
Abstract
Rapid and efficient synthesis of substituted 3-carboxylquinoline derivatives from 4-chloro-3-formylcoumarin and substituted anilines using 30% $H_2SO_4$ in methanol at room temperature within the duration of 5-30 min., through domino condensation-cyclization-ring opening reaction.
Keywords
3-Carboxylquinoline derivatives; 4-Chloro-3-formylcoumarin; Anilines;
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1 Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2001, 2576.
2 Takashi, M.; Ichikawa, J. Chem. Lett. 2004, 33, 590.   DOI
3 Jiang, B.; Si, Y.-G. J. Org. Chem. 2002, 67, 9449.   DOI
4 Cho, C. S.; Kim, T. K.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Organomet. Chem. 2002, 650, 65.   DOI
5 McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257.   DOI
6 Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.   DOI
7 Akiyama, T.; Nakashima, S.; Yokota, K.; Fuchibe, K. Chem. Lett. 2004, 33, 922.   DOI
8 Cho, C. S.; Oh, B. H.; Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000, 1885.
9 Sangu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 6, 353.   DOI
10 Mahata, P. K.; Venkatesh, C.; Kumar, U. K. S.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3966.   DOI
11 Yadav, J. S.; Reddy, B. V. S.; Rao, R. S.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610.
12 Yadav, J. S.; Reddy, B. V. S.; Premalatha, K. Synlett 2004, 963.
13 Yadav, J. S.; Reddy, B. V. S.; Sreedhar, R.; Rao, S.; Nagaiah, K. Synthesis 2004, 14, 2381.
14 De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 1647.   DOI
15 Zhang, X.; Yao, T.; Campo, M.A.; Larock, R.C. Tetrahedron Lett. 2010, 66, 1177.   DOI   ScienceOn
16 Subhas, B.; Idrees, D.; Jakka, M.; Venkateswara Rao, N. M. J. J. Comb. Chem. 2010, 12, 100.   DOI
17 Shan, G.; Sun, X.; Xia, Q.; Rao, Y. Org. Lett. 2011, 10.1021/ol202334s.   DOI
18 Schroeder, G.; Luttke, W. Chem. Ber. 1972, 105, 2175.   DOI
19 Palmer, M. H. J. Chem. Soc. 1962, 3645.   DOI
20 McNab, H.; Murray, E. A. J. Chem. Soc., Perkin Trans. 1 1988, 333.
21 McNab, H.; Murray, E. A. ARKIVOC 2002, iii, 95.
22 Robert, G. F. J. Comb. Chem. 2000, 1, 195.
23 Matsugi, M.; Tabusa, F.; Minamikawa, J. Tetrahedron Lett. 2000, 41, 8523.   DOI
24 Ranu, B. C.; Hajra, A.; Dey, S. S.; Jana, U. Tetrahedron 2003, 59, 813.   DOI
25 Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668.   DOI
26 Wu, Y.-C.; Li, L.; Li, H.-J.; Wang, D.; Chen, Y.-J. J. Org. Chem. 2006, 71, 6592.   DOI
27 Tanaka, S.-Y.; Yasuda, M.; Baba, A. J. Org. Chem. 2006, 71, 800.   DOI
28 Dieter Heber Arch. Pharma. (Weinheim) 1987, 320, 595.   DOI
29 Matsugi, M.; Tabusa, F.; Minamikawa, J.-I. Tetrahedron Lett. 2000, 41, 8523.   DOI
30 Panda, K.; Siddiqui, I.; Mahata, P. K.; Ila, H.; Junjappa, H. Synlett 2004, 449.
31 Ishikawa, T.; Manabe, S.; Aikawa, T.; Kudo, T.; Saito, S. Org. Lett. 2004, 6, 2361.   DOI
32 Zhao, F.; yang, X.; Liu, J. Tetrahedron 2004, 60, 9945.   DOI
33 Theeraladanon, C.; Arisawa, M.; Nishida, A.; Nakagawa, M. Tetrahedron 2004, 60, 3017.   DOI
34 Ichikawa, J.; Wada, Y.; Miyazaki, H.; Mori, T.; Kuroki, H. Org. Lett. 2003, 5, 1455.   DOI
35 Amii, H.; Kishikawa, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109.   DOI
36 Denny, W. A.; Wilson, W. R.; Ware, D. C.; Atwell, G. J.; Milbank, J. B.; Stevenson, R. J. U.S Patent, 7064117, 2006.
37 Mahamoud, A.; Chevalier, J.; Davin-Regli, A.; Barbe, J. Jean Marie Pages. Curr. Drug Targets. 2006, 7, 843.   DOI
38 Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Biol. Pharm. Bull. 2004, 27, 1683.   DOI
39 Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129.   DOI
40 Wilson, W. D.; Zhao, M.; Patterson, S. E.; Wydra, R. L.; Janda, L.; Strekowski, L. Med. Chem. Res. 1992, 1, 102.
41 Atwell, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1989, 32, 396.   DOI
42 Xia, Y.; Yang, Z. Y.; Xia, P.; Bastow, K. F.; Tachibana, Y.; Kuo, S. C.; Hamel, E.; Hackl, T.; Lee, K. H. J. Med. Chem. 1998, 41, 1155.   DOI   ScienceOn
43 Chen, Y. L.; Chen, I. L.; Tzeng, C. C.; Wang, T. C. Helv. Chim. Acta 2000, 83, 989.   DOI
44 Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315.   DOI   ScienceOn
45 Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 2001, 2491.
46 Julia, M. Ann. Chim. (France) 1950, 595.
47 Kouznetsov, V. V.; Mendez, L. Y.; Gomez, C. M. Curr. Org. Chem. 2005, 9(2), 141.   DOI
48 Chambers, R. D.; Holling, D.; Sandford, G.; Batsanov, A. S.; Howard, J. A. K. J. Fluorine Chem. 2004, 125, 661.   DOI
49 Konig, W. Ber. 1923, 56, 1853.   DOI
50 Gagan, J. M.; Lloyd, D. J. Chem. Soc., Chem. Commun. 1967, 1043.
51 Acheson, R. M.; Bolton, R. G. Tetrahedron Lett. 1973, 2827.
52 Nasveld, P.; Kitchener, S. Trans. R. Soc. Trop. Med. Hyg. 2005, 99, 2.   DOI
53 Leatham, P. A.; Bird, H. A.; Wright, V.; Seymour, D.; Gordon, A. Eur. J. Rheumatol. Inflamm. 1983, 6, 209.