Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.8.2446

An Expedient Synthesis of Oxindole Dimers by Direct Oxidative Dimerization of Oxindoles  

Lee, Hyun Ju (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Lee, Sangku (Immune Modulator Research Center, KRIBB)
Lim, Jin Woo (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Kim, Jae Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
Publication Information
Abstract
Oxindole dimers have been used as intermediates in the synthesis of various cyclotryptamine alkaloids. An efficient direct synthesis of oxindole dimers has been carried out from 3-substituted oxindoles via an oxidative dimerization using manganese(III) acetate or copper acetate/silver acetate system.
Keywords
Oxindole dimers; Oxidative dimerization; Manganese(III) acetate; Oxindoles;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Citterio, A.; Santi, R.; Fiorani, T.; Strologo, S. J. Org. Chem. 1989, 54, 2703-2712.   DOI
2 Nguyen, V.-H.; Nishino, H. Tetrahedron Lett. 2004, 45, 3373-3377.   DOI   ScienceOn
3 Du, Y.; Zhang, Y.; Wang, S.; Zhao, K. Synlett 2009, 1835-1841.
4 Periasamy, M.; Ramani, G.; Muthukumaragopal, G. P. Synthesis 2009, 1739-1743.
5 Matsumura, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809-2812.   DOI   ScienceOn
6 Frenette, M.; Aliaga, C.; Font-Sanchis, E.; Scaiano, J. C. Org. Lett. 2004, 6, 2579-2582.   DOI   ScienceOn
7 Cho, L. Y.; Romero, J. R. Tetrahedron Lett. 1995, 36, 8757-8760.   DOI   ScienceOn
8 Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem. Eur. J. 2009, 15, 7846-7849.   DOI   ScienceOn
9 Ishikura, M.; Takahashi, N.; Yamada, K.; Yanada, R. Tetrahedron 2006, 62, 11580-11591.   DOI   ScienceOn
10 Snider, B. B.; Vo, N. H.; Foxman, B. M. J. Org. Chem. 1993, 58, 7228-7237.   DOI   ScienceOn
11 Cao, S.-H.; Zhang, X.-C.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2011, 2668-2672.
12 Kobayashi, G.; Furukawa, S. Chem. Pharm. Bull. 1964, 12, 1129-1135.   DOI   ScienceOn
13 Grigg, R.; Whitney, S.; Sridharan, V.; Keep, A.; Derrick, A. Tetrahedron 2009, 65, 4375-4383.   DOI   ScienceOn
14 Lopez-Alvarado, P.; Avendano, C. Synthesis 2002, 104-110.
15 Albertshofer, K.; Tan, B.; Barbas, C. F., III. Org. Lett. 2012, 14, 1834-1837.   DOI   ScienceOn
16 Shimazawa, R.; Kuriyama, M.; Shirai, R. Bioorg. Med. Chem. Lett. 2008, 18, 3350-3353.   DOI   ScienceOn
17 Buckley, B. R.; Fernandez, D.-R. B. Tetrahedron Lett. 2013, 54, 843-846.   DOI   ScienceOn
18 Liu, Y.; Zhang, L.; Jia, Y. Tetrahedron Lett. 2012, 53, 684-687.   DOI   ScienceOn
19 Ghosh, S.; De, S.; Kakde, B. N.; Bhunia, S.; Adhikary, A.; Bisai, A. Org. Lett. 2012, 14, 5864-5867.   DOI   ScienceOn
20 Kukosha, T.; Trufilkina, N.; Katkevics, M. Synlett 2011, 2525-2528.
21 Munusamy, R.; Dhathathreyan, K. S.; Balasubramanian, K. K.; Venkatachalam, C. S. J. Chem. Soc., Perkin Trans. 2 2001, 1154-1166.
22 Overman, L. E.; Larrow, J. F.; Stearns, B. A.; Vance, J. M. Angew. Chem. Int. Ed. 2000, 39, 213-215.   DOI
23 Lee, H. J.; Kim, K. H.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2013, 54, 170-175.   DOI   ScienceOn
24 Shang, Y.; Jie, X.; Zhou, J.; Hu, P.; Huang, S.; Su, W. Angew. Chem. Int. Ed. 2013, 52, 1299-1303.   DOI   ScienceOn
25 Moon, Y.; Kwon, D.; Hong, S. Angew. Chem. Int. Ed. 2012, 51, 11333-11336.   DOI   ScienceOn
26 Diao, T.; Wadzinski, T. J.; Stahl, S. S. Chem. Sci. 2012, 3, 887-891.   DOI
27 Izawa, Y.; Pun, D.; Stahl, S. S. Science 2011, 333, 209-213.   DOI   ScienceOn
28 Diao, T.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 14566-14569.   DOI   ScienceOn
29 Kozlowski, M. C.; DiVirgilio, E. S.; Malolanarasimhan, K.; Mulrooney, C. A. Tetrahedron: Asymmetry 2005, 16, 3599-3605.   DOI   ScienceOn
30 Tokunaga, M.; Harada, S.; Iwasawa, T.; Obora, Y.; Tsuji, Y. Tetrahedron Lett. 2007, 48, 6860-6862.   DOI   ScienceOn
31 Lee, D. J.; Kim, K.; Park, Y. J. Org. Lett. 2002, 4, 873-876.   DOI   ScienceOn
32 Do, H.-Q.; Tran-Vu, H.; Daugulis, O. Organometallics 2012, 31, 7816-7818.   DOI   ScienceOn
33 de Jongh, H. A. P.; de Jonge, C. R. H. I.; Mijs, W. J. J. Org. Chem. 1971, 36, 3160-3168.   DOI
34 de Jongh, H. A. P.; de Jonge, C. R. H. I.; Sinnige, H. J. M.; de Klein, W. J.; Huysmans, W. G. B.; Mijs, W. J.; van den Hoek, W. J.; Smidt, J. J. Org. Chem. 1972, 37, 1960-1966.   DOI
35 Snider, B. B.; Smith, R. B. Tetrahedron 2002, 58, 25-34.   DOI   ScienceOn
36 Snider, B. B.; Patricia, J. J.; Kates, S. A. J. Org. Chem. 1988, 53, 2137-2143.   DOI
37 Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702-7703.   DOI   ScienceOn
38 Guo, C.; Song, J.; Huang, J.-Z.; Chen, P.-H.; Luo, S.-W.; Gong, L.-Z. Angew. Chem. Int. Ed. 2012, 51, 1046-1050.   DOI   ScienceOn
39 Mitsunuma, H.; Shibasaki, M.; Kanai, M.; Matsunaga, S. Angew. Chem. Int. Ed. 2012, 51, 5217-5221.   DOI   ScienceOn
40 Overman, L. E.; Peterson, E. A. Angew. Chem. Int. Ed. 2003, 42, 2525-2528.   DOI   ScienceOn
41 Link, J. T.; Overman, L. E. J. Am. Chem. Soc. 1996, 118, 8166-8167.   DOI   ScienceOn
42 Fang, C.-L.; Horne, S.; Taylor, N.; Rodrigo, R. J. Am. Chem. Soc. 1994, 116, 9480-9486.   DOI
43 Inada, A.; Morita, Y. Heterocycles 1982, 19, 2139-2142.   DOI
44 Ellis, J. M.; Overman, L. E.; Tanner, H. R.; Wang, J. J. Org. Chem. 2008, 73, 9151-9154.   DOI   ScienceOn