Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.10.2968

Montmorillonite Clay Catalyzed Three Component, One-Pot Synthesis of 5-Hydroxyindole Derivatives  

Reddy, B.V. Subba (Natural Product Chemistry, Indian Institute of Chemical Technology)
Reddy, P. Sivaramakrishna (Natural Product Chemistry, Indian Institute of Chemical Technology)
Reddy, Y. Jayasudhan (Natural Product Chemistry, Indian Institute of Chemical Technology)
Bhaskar, N. (Natural Product Chemistry, Indian Institute of Chemical Technology)
Reddy, B. Chandra Obula (Natural Product Chemistry, Indian Institute of Chemical Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.10, 2013 , pp. 2968-2972 More about this Journal
Abstract
A highly efficient and environmentally benign protocol has been developed for the first time to produce a wide range of biologically active 5-hydroxyindole derivatives using montmorillonite KSF clay as a reusable solid acid catalyst. The use of recyclable clay makes this procedure quite simple, more convenient and cost-effective.
Keywords
3CC reaction; Solid acid catalysis; Nenitzescu reaction; 5-Hydroxyindole;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Nenitzescu, C. Chem. Zentralbl. 1929, 2331.
2 Parr, R. W.; Reiss, J. A. Aust. J. Chem. 1984, 37, 1263.   DOI
3 Pawlak, J. M.; Khau, V. V.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem, 1996, 61, 9055.   DOI   ScienceOn
4 Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253.   DOI   ScienceOn
5 Neumann, J. J.; Rakshit, S.; Drcge, T.; Wurtz, S.; Glorius, F. Chem. Eur. J. 2011, 17, 7298.   DOI   ScienceOn
6 Clark, J. H. Acc. Chem. Res. 2002, 35, 791.   DOI   ScienceOn
7 Balogh, M.; Laszlo, P. In Organic Chemistry Using Clay; Spinger-Verlag: New York, 1993.
8 Laszlo, P. Science 1987, 235, 1473.   DOI   ScienceOn
9 Laszlo, P. Pure Appl. Chem. 1990, 62, 2027.   DOI
10 Cornelis, A.; Laszlo, P. Synlett 1994, 155.
11 Yadav, J. S.; Reddy, B. V. S.; Sunitha, V.; Reddy, K. S.; Ramakrishna, K. V. S. Tetrahedron Lett. 2004, 45, 7947.   DOI   ScienceOn
12 Yadav, J. S.; Reddy, B. V. S.; Satheesh, G. Tetrahedron Lett. 2004, 45, 3673.   DOI   ScienceOn
13 Yadav, J. S.; Reddy, B. V. S.; Sadasiv, K.; Reddy, P. S. R. Tetrahedron Lett. 2002, 43, 3853.   DOI   ScienceOn
14 Yadav, J. S.; Reddy, B. V. S.; Kumar, G. M.; Murthy, Ch. V. S. R. Tetrahedron Lett. 2001, 42, 89.   DOI   ScienceOn
15 Li, S. M. Nat. Prod. Rep. 2010, 27, 57.   DOI   ScienceOn
16 Weng, J. R.; Tsai, C. H.; Kulp, S. K.; Chen, C. S. Cancer Lett. 2008, 262, 153.   DOI   ScienceOn
17 Rieck, G. C.; Fiander, A. N. Mol. Nutr. Food Res. 2008, 52, 105.   DOI   ScienceOn
18 Brancale, A.; Silvestri, R. Med. Res. Rev. 2007, 27, 209.   DOI   ScienceOn
19 Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73.   DOI   ScienceOn
20 McKay, M. J.; Carroll, A. R.; Quinn, R. J.; Hooper, J. N. A. J. Nat. Prod. 2002, 65, 595.   DOI   ScienceOn
21 Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell Science; Oxford, 2000.
22 Sundberg, R. J. Indoles; Academic Press: London, 1996.
23 Ishikura, M.; Yamada, K. Nat. Prod. Rep. 2009, 26, 803.   DOI   ScienceOn
24 Higuchi, K.; Kawasaki, T. Nat. Prod. Rep. 2007, 24, 843.   DOI   ScienceOn
25 Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761.   DOI   ScienceOn
26 Shefali, S.; Srivastava, S. K.; Husbands, S. M.; Lewis, J. W. J. Med. Chem. 2005, 48, 635.   DOI   ScienceOn
27 Walker, S. R.; Carter, E. J.; Huff, B. C.; Morris, J. C. Chem. Rev. 2009, 109, 3080.   DOI   ScienceOn
28 Leblanc, Y.; Black, W. C.; Chan, C. C.; Charleson, S.; Delorme, D.; Denis, D.; Bayly, C.; Gauthier, J.Y.; Grimm, R.; Gordon, R.; Guay, D.; Hamel, P.; Kargman, S.; Lau, C. K.; Mancini, J.; Ouellet, M.; Percival, D.; Roy, P.; Skorey, K.; Tagari, P.; Vickers, P.; Wong, E.; Xu, L.; Prasit, P. Bioorg. Med. Chem. Lett. 1996, 6, 731.   DOI   ScienceOn
29 Pawlak, J. M.; Khau, V. V.; Hutchinson, D. R.; Martinelli, M. J. Org. Chem. 1996, 61, 9055.   DOI   ScienceOn
30 Landwehr, J.; George, S.; Karg, E. M.; Poeckel, D.; Steinhilber, D.; Troschuetz, R.; Werz, O. J. Med. Chem. 2006, 49, 4327.   DOI   ScienceOn
31 Karg, E. M.; Luderer, S.; Pergola, C.; Buhring, U.; Rossi, A.; Northoff, H.; Sautebin, L.; Troschutz, R.; Werz, O. J. Med. Chem. 2009, 52, 3474.   DOI   ScienceOn
32 Kevin, H.; Aurelien, G. J. C.; Shengze, Z.; John, A. M. Tetrahedron Lett. 2009, 50, 3290.   DOI   ScienceOn
33 Goh, W. K.; Black, D. C.; Kumar, N. Tetrahedron Lett. 2007, 48, 9008.   DOI   ScienceOn
34 Dalpozzo, R.; Bartoli, G. Curr. Org. Chem. 2005, 9, 163.   DOI   ScienceOn
35 Chintakunta, R.; Verrababurao, K.; Raju, B. R.; Kuo, C.; Yao, C. F. Tetrahedron Lett. 2009, 50, 4037.   DOI   ScienceOn
36 Ghanamani, S.; Paramasivan, T. P. Tetrahedron Lett. 2009, 50, 3959.   DOI   ScienceOn
37 Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
38 Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.   DOI   ScienceOn
39 Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Afonso, C. A. M.; Trindade, A. F. Chem. Rev. 2009, 109, 2703.   DOI   ScienceOn