7702
W.-M. Dai et al. / Tetrahedron Letters 43 (2002) 7699–7702
furnished the C4 arenesulfamoylindoles 10d-1 and 10d-
2 in 75–83% yields (Scheme 3 and Table 1, entries 9 and
10).
Rep. Med. Chem.; Bristol, J. A., Ed.; Academic Press:
San Diego, 1997; Vol. 32, p. 92; (b) Galatsis, P. In Ann.
Rep. Med. Chem.; Bristol, J. A., Ed.; Academic Press:
San Diego, 1997; Vol. 32, p. 321.
In summary, we have developed a general synthesis of
indoles possessing a nitrogen substituent at the C4, C5,
C6, and C7 positions from the commercially available
nitro 2-aminophenols 4a–c and 2-chloro-1,3-dinitroben-
zene 11. Introduction of diversity at the C2 position can
be achieved by using commercially available 1-alkynes.
Our synthesis is of interest for the generation of indole
libraries. Work toward this goal is currently in progress
in our laboratory.
4. Robichaud, A. J.; Largent, B. L. In Ann. Rep. Med.
Chem.; Doherty, A. M., Ed.; Academic Press: San Diego,
2000; Vol. 35, p. 13.
5. Li, Q.; Sham, H. L.; Rosenberg, S. H. In Ann. Rep. Med.
Chem.; Doherty, A. M., Ed.; Academic Press: San Diego,
1999; Vol. 34, pp. 145–146.
6. Dai, W.-M.; Guo, D.-S.; Sun, L.-P. Tetrahedron Lett.
2001, 42, 5275–5278.
7. All new compounds are fully characterized by IR, 1H
NMR, 13C NMR and MS.
8. Dai, W.-M.; Cheung, Y. K.; Tang, K. W.; Choi, P. Y.;
Chung, S. L. Tetrahedron 1995, 51, 12263–12276.
9. Dai, W.-M.; Wu, J. Tetrahedron 1997, 53, 9107–9114.
10. Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P.
Angew. Chem., Int. Ed. 2000, 39, 2488–2490.
11. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G.
C. Org. Lett. 2000, 2, 1729–1731.
12. Bellamy, F. D.; Ou, K. Tetrahedron Lett. 1984, 25,
839–842.
Acknowledgements
This work is supported by the Innovation and Technol-
ogy Fund (ITS/119/00) from the Innovation and Tech-
nology Commission of the Hong Kong Special
Administration Region, China. We also thank HKUST
for providing a Post Doctoral Fellowship Matching
Fund to D.-S. Guo.
13. (a) Castro, C. E.; Stephens, R. D. J. Org. Chem. 1963, 28,
2163; (b) Castro, C. E.; Gauhan, E. J.; Owsley, D. C. J.
Org. Chem. 1966, 31, 4071–4078; (c) Villemin, D.;
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Kumar, V.; Dority, A. A.; Bacon, E. R.; Singh, B.;
Lesher, G. Y. J. Org. Chem. 1992, 57, 6995–6998; (e)
Katritzky, A. R.; Li, J.; Stevens, C. V. J. Org. Chem.
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