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http://dx.doi.org/10.5012/bkcs.2012.33.1.43

An Efficient Synthesis of Substituted Quinolines via Indium(III) Chloride Catalyzed Reaction of Imines with Alkynes  

Zhu, Mei (College of Chemistry and Chemical Engineering, Luoyang Normal University)
Fu, Weijun (College of Chemistry and Chemical Engineering, Luoyang Normal University)
Xun, Chen (College of Chemistry and Chemical Engineering, Luoyang Normal University)
Zou, Guanglong (School of Chemistry and Environmental Science, Guizhou University for Nationalities)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.1, 2012 , pp. 43-47 More about this Journal
Abstract
An efficient synthetic method for the preparation of quinolines through indium(III) chloride-catalyzed tandem addition-cyclization-oxidation reactions of imines with alkynes was developed. The processes can provide a diverse range of quinoline derivatives in good yields from simple imines and alkynes.
Keywords
Indium(III); Quinoline; Imine; Alkyne;
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Times Cited By Web Of Science : 2  (Related Records In Web of Science)
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1 Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668.   DOI   ScienceOn
2 Kobayashi, K.; Takanohashi, A.; Watanabe, S.; Morikawa, O.; Konishi, H. Tetrahedron Lett. 2000, 41, 7657.   DOI   ScienceOn
3 Case, F.; Buck, C. J. Org. Chem. 1956, 21, 697.   DOI
4 Palimkar, S. S.; Siddiqui, S. A.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. J. Org. Chem. 2003, 68, 9371.   DOI   ScienceOn
5 Michael, J. P. Nat. Prod. Rep. 1997, 14, 605.   DOI   ScienceOn
6 Auge, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739.
7 Dong, Q. L.; Liu, G. S.; Zhou, H. B.; Chen, L.; Yao, Z. J. Tetrahedron Lett. 2008, 49, 1636.   DOI   ScienceOn
8 Akiyama, T.; Nakashima, S.; Yokota, K.; Fuchibe, K. Chem. Lett. 2004, 33, 922.   DOI   ScienceOn
9 Nair, V.; Ros, S.; Jayan; C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959.   DOI   ScienceOn
10 Ranu, B. C. Eur. J. Org. Chem. 2000, 2347.
11 Lee, P. H. Bull. Korean Chem. Soc. 2007, 28, 17.   DOI   ScienceOn
12 Teo, Y. C.; Loh, T. P. Org. Lett. 2005, 7, 2539.   DOI   ScienceOn
13 Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291.   DOI   ScienceOn
14 Loh, T. P.; Wei, L. L. Tetrahedron Lett. 1998, 39, 323.   DOI   ScienceOn
15 Friestad, G. K.; Korapala, C. S.; Ding, H. J. Org. Chem. 2006, 71, 281.   DOI   ScienceOn
16 Seomoon, D. A. J.; Lee, P. H. Org. Lett. 2009, 11, 2401.   DOI   ScienceOn
17 Onishi, Y.; Ogawa, D.; Yasuda, M.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13690.   DOI   ScienceOn
18 Yasuda, M.; Saito, T.; Ueba, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 43, 1414.   DOI   ScienceOn
19 Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212.   DOI   ScienceOn
20 Miura, K.; Fujisawa, N.; Hosomi, A. J. Org. Chem. 2004, 69, 2427.   DOI   ScienceOn
21 Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.   DOI   ScienceOn
22 Yasuda, M.; Saito, T.; Ueba, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 43, 1414.   DOI   ScienceOn
23 Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Miyamura, T.; Shirakawa, E. J. Am. Chem. Soc. 2008, 130, 15823.   DOI   ScienceOn
24 Fu, W. J.; Xu, C.; Zou, G.; Hong, D.; Deng, D.; Wang, Z.; Ji, B. Synlett 2009, 763.
25 Huang, X.; Fu, W. J. Tetrahedron Lett. 2008, 49, 2359.   DOI   ScienceOn
26 Fu, W. J.; Huang, X. Tetrahedron Lett. 2008, 49, 562.   DOI   ScienceOn
27 Kulkarni, A.; Torok, B. Green Chem. 2010, 12, 875.   DOI   ScienceOn
28 Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G.; Ruggieri, F. J. Org. Chem. 1992, 57, 1842.   DOI
29 Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanrdi, G. J. Chem. Soc. Chem. Comm. 1984, 1320.
30 Li, X.; Mao, Z.; Wang, Y.; Chen, W.; Lin, X. Tetrahedron 2011, 67, 3858.   DOI   ScienceOn
31 Majumdar, K. C.; Ponra, S.; Ghosh, D.; Taher, A. Synlett 2011, 104.
32 Yadav, J. S.; Reddy, B. V. S.; Srinivasa Rao, R.; Naveenkumar, V.; Nagaiah, K. Synthesis 2003, 1610.
33 Zhao, Y.; Zhang, W.; Wang, S.; Liu, Q. J. Org. Chem. 2007, 72, 4985.   DOI   ScienceOn
34 Gaddam, V.; Ramesh, S.; Nagarajan, R. Tetrahedron 2010, 66, 4218.   DOI   ScienceOn
35 Guchhait, S. K.; Jadeja, K.; Madaan, C. Tetrahedron Lett. 2009, 50, 6861.   DOI   ScienceOn
36 Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2009, 74, 5476.   DOI   ScienceOn
37 Zhang, J.; Yang, W.; Song, L.; Cai, X.; Zhu, S. Tetrahedron Lett. 2004, 45, 5771.   DOI   ScienceOn
38 Amii, H.; Kishikawa, Y.; Uneyama, K. Org. Lett. 2001, 3, 1109.   DOI   ScienceOn
39 Jiang, B.; Si, Y. G. J. Org. Chem. 2002, 67, 9449.   DOI   ScienceOn
40 Liu, X. Y.; Ding, P.; Huang, J. S.; Che, C. M. Org. Lett. 2007, 9, 2645.   DOI   ScienceOn
41 Lekhok, K. C.; Prajapati, D.; Boruah, R. C. Synlett 2008, 655.
42 Sakai, N.; Annaka, K.; Konakahara, T. J. Org. Chem. 2006, 71, 3653.   DOI   ScienceOn
43 Yanada, R.; Hashimoto, K.; Tokizane, T.; Miwa, Y.; Minami, H.; Yanada, K.; Ishikura, M.; Takemoto, Y. J. Org. Chem. 2008, 73, 5135.   DOI   ScienceOn
44 Sakai, N.; Annaka, K.; Fujita, A.; Sato, A.; Konakahara, T. J. Org. Chem. 2008, 73, 4160.   DOI   ScienceOn
45 Loh, T. P.; Chua, G. L. Chem. Commun. 2006, 2739.
46 Cintas, P. Synlett 1995, 1087.
47 Podlech, J.; Maier, T. C. Synthesis 2003, 633.
48 Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 68, 467.   DOI   ScienceOn
49 Gladiali, S.; Chelucci, G.; Mudadu, M. S.; Gastaut, M. A.; Thummel, R. P. J. Org. Chem. 2001, 66, 400.   DOI   ScienceOn
50 Breitmaier, E.; Gassenmann, S.; Bayer, E. Tetrahedron 1970, 26, 5907.   DOI   ScienceOn
51 Martinez, R.; Ramon, D. J.; Yus, M. J. Org. Chem. 2008, 73, 9778.   DOI   ScienceOn
52 Huo, Z.; Gridnev, L. D.; Yamamoto, Y. J. Org. Chem. 2010, 75, 1266.   DOI   ScienceOn
53 Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763.   DOI   ScienceOn
54 Korivi, R. P.; Cheng, C. H. J. Org. Chem. 2006, 71, 7079.   DOI   ScienceOn
55 Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 4592.   DOI   ScienceOn
56 Cao, K.; Zhang, F. M.; Tu, Y. Q.; Zhou, X. T.; Fan. C. A. Chem. Eur. J. 2009, 15, 6332.   DOI   ScienceOn
57 Zhang, Y.; Li, P.; Wang, L. J. Heterocyclic Chem. 2011, 48, 153.   DOI   ScienceOn
58 Xiao, F.; Chen, Y.; Liu, Y.; Wang, J. Tetrahedron 2008, 64, 2755.   DOI   ScienceOn
59 Abbiati, G.; Arcadi, A.; Marinelli, F.; Rossi, E.; Verdecchia, M. Synlett 2006, 3218.
60 Ock, S. K.; Youn, S. W. Bull. Korean Chem. Soc. 2010, 31, 704.   DOI   ScienceOn
61 Xie, H.; Zhu, J.; Chen, Z.; Li, S.; Wu, Y. Synlett 2010, 2659.
62 Saito, A.; Kasai, J.; Konishi, T.; Hanzawa, Y. J. Org. Chem. 2010, 75, 6980.   DOI   ScienceOn
63 Desrat, S.; Weghe, P. J. Org. Chem. 2009, 74, 6728.   DOI   ScienceOn
64 Kuninobu, Y.; Inoue, Y.; Takai, K. Chem. Lett. 2007, 36, 1422.   DOI   ScienceOn
65 Bortolotti, B.; Leardini, R.; Nanni, D.; Zanardi, G. Tetrahedron 1993, 49, 10157.   DOI   ScienceOn
66 Bortolotti, B.; Leardini, R.; Nanni, D.; Zanrdi, G. Tetrahedron 1993, 49, 10157.   DOI   ScienceOn
67 Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 1021.
68 Narasaka, K.; Shibata, T. Heterocycles 1993, 35, 1039.   DOI   ScienceOn
69 Larsen, R. D.; Corley, E. G.; King, A. O.; Carrol, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J.; Labelle, M.; Gauthier, J. Y.; Xiang, Y. B.; Zamboni, R. J. J. Org. Chem. 1996, 61, 3398.   DOI   ScienceOn
70 Chen, Y. L.; Fang, K. C.; Sheu, J. Y.; Hsu, S. L.; Tzeng, C. C. J. Med. Chem. 2001, 44, 2374.   DOI   ScienceOn
71 Sawada, Y.; Kayakiri, H.; Abe, Y.; Imai, K.; Katayama, A.; Oku, T.; Tanaka, H. J. Med. Chem. 2004, 47, 1617.   DOI   ScienceOn
72 Groisy- Delcey, M.; Groisy, A.; Carrez, D.; Huel, C.; Chaironi, A.; Ducrot, P.; Bisagni, E.; Jin, L.; Leclercq, G. Bioorg. Med. Chem. 2000, 8, 2629.   DOI   ScienceOn
73 Strekowski, L.; Say, M.; Henary, M.; Ruiz, P.; Manzel, L.; Macfarlane, D. E.; Bojarski, A. J. J. Med. Chem. 2003, 46, 1242.   DOI   ScienceOn
74 Jenekhe, S. A.; Lu, L.; Alam, M. M. Macromolecules 2001, 34, 7315.   DOI   ScienceOn
75 Jegou, G.; Jenekhe, S. A. Macromolecules 2001, 34, 7926.   DOI   ScienceOn
76 Agrawal, A. K.; Jenekhe, S. A. Chem. Mater. 1996, 8, 579.   DOI   ScienceOn
77 Jenekhe, S. A.; Zhang, X.; Chen, X. L.; Choong, V. E.; Gao, Y.; Hsieh, B. R. Chem. Mater. 1997, 9, 409.   DOI   ScienceOn
78 Zhang, X.; Shetty, A. S.; Jenekhe, S. A. Macromolecules 2000, 33, 2069.   DOI   ScienceOn
79 Curran, A. C. W. J. Chem. Soc., Perkin Trans. 1 1976, 975.
80 Misani, F.; Bogert, M. T. J. Org. Chem. 1945, 10, 347.   DOI
81 Sakai, N.; Aoki, D.; Hamajima, T.; Konakahara, T. Tetrahedron Lett. 2006, 47, 1261.   DOI   ScienceOn