Browse > Article
http://dx.doi.org/10.5012/bkcs.2014.35.10.2950

Indium(III) Chloride Mediated Michael Addition of Indoles to Ketene S,S-Acetals: Synthesis of Bis- and Tris-indolylketones  

Singh, Thokchom Prasanta (Department of Chemistry, Manipur University)
Khan, Ruhima (Department of Chemistry, Manipur University)
Noh, Young Ri (Department of Chemistry, Research Institute of Natural Science (RINS), Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Lee, Sang-Gyeong (Department of Chemistry, Research Institute of Natural Science (RINS), Graduate School for Molecular Materials and Nanochemistry, Gyeongsang National University)
Singh, Okram Mukherjee (Department of Chemistry, Manipur University)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.10, 2014 , pp. 2950-2954 More about this Journal
Abstract
A series of bis and tris-indolylketones and meridianin alkaloids are prepared by one pot Michael reaction of indole and ketene S,S-acetals under solvent-free condition using mild Lewis acid $InCl_3$.
Keywords
Bis-indolylketones; Tris-indolylketones; One-pot; Solvent-free; Michael reaction;
Citations & Related Records
연도 인용수 순위
  • Reference
1 (b) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.   DOI   ScienceOn
2 (b) Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1.   DOI   ScienceOn
3 (a) Gilchrist, T. L. J. Chem. Soc. Perkin Trans. 1 2001, 20, 2491.
4 Yang, C.-G.; Huang, H.; Jiang, B. Curr. Org. Chem. 2004, 8, 1691.   DOI
5 (a) Roy, A.; Bosedasgupta, S.; Ganguly, A.; Jaisankar, P.; Majumder, H. K. Antimicrob. Agents Chemother. 2009, 53, 2589.   DOI
6 (b) Safe, S.; Papineni, S.; Chintharlapalli, S. Cancer Lett. 2008, 269, 326.   DOI
7 Singh, H.; Singh, K. Tetrahedron 1988, 44, 5897.   DOI
8 Sashidhara, K. V.; Kumar, M.; Sonkar, R.; Singh, B. S.; Khannaand, A. K.; Bhatia, G. J. Med. Chem. 2012, 55, 2769.   DOI
9 (a) Benabadji, S. H.; Wen, R.; Zheng, J.; Dong, X.; Yuan, S. Acta Pharmacol. Sin. 2004, 25, 666.
10 (b) Praveen, C.; Kumar, P. D.; Muralidharan, D.; Perumal, P. T. Bioorg. Med. Chem. Lett. 2010, 24, 7292.
11 Li, J.; Guang, B.; Wang, L.; Li, B.; Zhang, G. Heterocycles 2003, 60, 1307.   DOI
12 (a) Boyarskikh, V.; Nyong, A.; Rainier, J. D. Angew. Chem. Int. Ed. 2008, 47, 5374.   DOI
13 (b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.   DOI
14 (c) Cadierno, V.; Francos, J.; Gimeno, J. Chem. Commun. 2010, 4175.
15 (a) Pan, L.; Bi, X.; Liu. Q. Chem. Soc. Rev. 2013, 42, 1251.   DOI   ScienceOn
16 Singh, T. P.; Bhattarcharya, S.; Singh, O. M. Org. Lett. 2013, 15, 1974.   DOI   ScienceOn
17 Yu, H.; Yu, Z. Angew. Chem. Int. Ed. 2009, 48, 2929.   DOI
18 Yu, H.; Li, T.; Liao, P. Synthesis 2012, 44, 3743.   DOI
19 (b) Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.   DOI   ScienceOn
20 (c) Ila, H.; Junjappa, H.; Mohanta, P. K. Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: New York, 2001; p 1.
21 (d) Misra, N. C.; Ila, H. J. Org. Chem. 2010, 75, 5195.   DOI
22 (c) Singh, O. M.; Devi, N. S. J. Org. Chem. 2009, 74, 3141.   DOI   ScienceOn
23 (e) Yadav, A. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1388.   DOI
24 (a) Devi, N. S.; Singh, S. J.; Singh, O. M. Synlett 2012, 23, 2111.   DOI   ScienceOn
25 (b) Devi, L. R.; Singh, O. M. Indian J. Chem: B 2012, 9, 1426.
26 (d) Singh, O. M.; Singh, S. J.; Devi, M. B.; Devi, L. N.; Singh, N. I.; Lee, S. G. Bioorg. Med. Chem. Lett. 2008, 18, 6462.   DOI
27 Veluri, R.; Oka, I.; Wagner-Dobler, I.; Laatsch, H. J. Nat. Prod. 2003, 66, 1520.   DOI
28 (a) Sundberg, R. J. Indoles; Academic Press: New York, USA, 1996.