Regioselective synthesis of 2,3,5-trisubstituted indoles from p-sulfinylaniline by dual use of the sulfinyl group

Heterocycles

Volumn 58, Issue , 2002, Pages 75-78

  Akai, Shuji ^a   Kawashita, Norihito ^a   Morita, Nobuyoshi ^a   Nakamura, Yuka ^a   Iio, Kiyosei ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 SULFINYLANILINE; ANILINE DERIVATIVE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0037159757     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. For recent reviews, see: R. J. Sundberg, 'Indoles,' Academic Press, London, 1996. M. Toyota and M. Ihara, Nat. Prod. Rep., 1998, 327. M. Somei, Heterocycles, 1999, 50, 1157. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 2000, 1045.
2. For recent reviews, see: R. J. Sundberg, 'Indoles,' Academic Press, London, 1996. M. Toyota and M. Ihara, Nat. Prod. Rep., 1998, 327. M. Somei, Heterocycles, 1999, 50, 1157. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 2000, 1045.
3. For recent reviews, see: R. J. Sundberg, 'Indoles,' Academic Press, London, 1996. M. Toyota and M. Ihara, Nat. Prod. Rep., 1998, 327. M. Somei, Heterocycles, 1999, 50, 1157. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 2000, 1045.
4. For recent reviews, see: R. J. Sundberg, 'Indoles,' Academic Press, London, 1996. M. Toyota and M. Ihara, Nat. Prod. Rep., 1998, 327. M. Somei, Heterocycles, 1999, 50, 1157. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 2000, 1045.
5. H. Tohma, H. Watanabe, S. Takizawa, T. Maegawa, and Y. Kita, Heterocycles, 1999, 51, 1785. T. A. Engler, W. Chai, and K. O. LaTessa, J. Org. Chem., 1996, 61, 9297. P. Dalidowicz and J. S. Swenton, J. Org. Chem., 1993, 58, 4802.
6. H. Tohma, H. Watanabe, S. Takizawa, T. Maegawa, and Y. Kita, Heterocycles, 1999, 51, 1785. T. A. Engler, W. Chai, and K. O. LaTessa, J. Org. Chem., 1996, 61, 9297. P. Dalidowicz and J. S. Swenton, J. Org. Chem., 1993, 58, 4802.
7. H. Tohma, H. Watanabe, S. Takizawa, T. Maegawa, and Y. Kita, Heterocycles, 1999, 51, 1785. T. A. Engler, W. Chai, and K. O. LaTessa, J. Org. Chem., 1996, 61, 9297. P. Dalidowicz and J. S. Swenton, J. Org. Chem., 1993, 58, 4802.
8. (a) A. Finaru, A. Berthault, T. Besson, G. Guillaumet, and S. Berteina-Raboin, Tetrahedron Lett., 2002, 43, 787 and references cited therein.
9. (b) F. Ujjainwalla and T. F. Walsh, Tetrahedron Lett., 2001, 42, 6441.
10. (c) B. R. Kenke, K. K. Adkison, S, G. Blanchard, L. M. Leesnitzer, R. A. Mook, Jr., K. D. Plunket, J. A. Ray, C. Roberson, R. Unwalla, and T. M. Willson, Bioorg. Med. Chem. Lett., 1999, 9, 3329.
11. (d) J. E. Audia, D. A. Evrard, G. R. Murdoch, J. J. Droste, J. S. Nissen, K. W. Schenck, P. Fludzinski, V. L. Lucaites, D. L. Nelson, and M. L. Cohen, J. Med. Chem., 1996, 39, 2773.
12. (e) F. D. King, A. M. Brown, L. M. Gaster, A. J. Kaumann, A. D. Medhurst, S. G. Parker, A. A. Parsons, T. L. Patch, and P. Raval, J. Med. Chem., 1993, 36, 1918.
13. Y. Murakami, M. Tani, K. Tanaka, and Y. Yokoyama, Chem. Pharm. Bull., 1988, 36, 2023. S. Hirano, R. Akai, Y. Shinoda, and S. Nakatsuka, Heterocycles, 1995, 41, 255.
14. Y. Murakami, M. Tani, K. Tanaka, and Y. Yokoyama, Chem. Pharm. Bull., 1988, 36, 2023. S. Hirano, R. Akai, Y. Shinoda, and S. Nakatsuka, Heterocycles, 1995, 41, 255.
15. T. Y. H. Wu, S. Ding, N. S. Gray, and P. G. Schultz, Org. Lett., 2001, 3, 3827.
16. S. Akai, Y. Takeda, K. Iio, K. Takahashi, N. Fukuda, and Y. Kita, J. Org. Chem., 1997, 62, 5526. Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, and S. Akai, Angew. Chem., Int. Ed. Engl., 1997, 36, 1529. Y. Kita, K. Iio, K. Kawaguchi, N. Fukuda, Y. Takeda, H. Ueno, R. Okunaka, K. Higuchi, T. Tsujino, H. Fujioka, and S. Akai, Chem. Eur. J., 2000, 6, 3897. S. Akai, T. Tsujino, N. Fukuda, K. Iio, Y. Takeda, K. Kawaguchi, T. Naka, K. Higuchi, and Y. Kita, Org. Lett., 2001, 3, 4015.
17. S. Akai, Y. Takeda, K. Iio, K. Takahashi, N. Fukuda, and Y. Kita, J. Org. Chem., 1997, 62, 5526. Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, and S. Akai, Angew. Chem., Int. Ed. Engl., 1997, 36, 1529. Y. Kita, K. Iio, K. Kawaguchi, N. Fukuda, Y. Takeda, H. Ueno, R. Okunaka, K. Higuchi, T. Tsujino, H. Fujioka, and S. Akai, Chem. Eur. J., 2000, 6, 3897. S. Akai, T. Tsujino, N. Fukuda, K. Iio, Y. Takeda, K. Kawaguchi, T. Naka, K. Higuchi, and Y. Kita, Org. Lett., 2001, 3, 4015.
18. S. Akai, Y. Takeda, K. Iio, K. Takahashi, N. Fukuda, and Y. Kita, J. Org. Chem., 1997, 62, 5526. Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, and S. Akai, Angew. Chem., Int. Ed. Engl., 1997, 36, 1529. Y. Kita, K. Iio, K. Kawaguchi, N. Fukuda, Y. Takeda, H. Ueno, R. Okunaka, K. Higuchi, T. Tsujino, H. Fujioka, and S. Akai, Chem. Eur. J., 2000, 6, 3897. S. Akai, T. Tsujino, N. Fukuda, K. Iio, Y. Takeda, K. Kawaguchi, T. Naka, K. Higuchi, and Y. Kita, Org. Lett., 2001, 3, 4015.
19. S. Akai, Y. Takeda, K. Iio, K. Takahashi, N. Fukuda, and Y. Kita, J. Org. Chem., 1997, 62, 5526. Y. Kita, Y. Takeda, M. Matsugi, K. Iio, K. Gotanda, K. Murata, and S. Akai, Angew. Chem., Int. Ed. Engl., 1997, 36, 1529. Y. Kita, K. Iio, K. Kawaguchi, N. Fukuda, Y. Takeda, H. Ueno, R. Okunaka, K. Higuchi, T. Tsujino, H. Fujioka, and S. Akai, Chem. Eur. J., 2000, 6, 3897. S. Akai, T. Tsujino, N. Fukuda, K. Iio, Y. Takeda, K. Kawaguchi, T. Naka, K. Higuchi, and Y. Kita, Org. Lett., 2001, 3, 4015.
20. We have reported a novel synthesis of diversely substituted benzofuran neolignans from p-sulfinylphenols by dual use of the single p-sulfinyl group, see: S. Akai, N. Morita, K. Iio, Y. Nakamura, and Y. Kita, Org. Lett., 2000, 2, 2279.
21. 2Ph) did not give the expected products (3).
22. The N-protected p-sulfinylanilines (1a and 1b) were prepared from commercial p-iodoaniline in three steps.
23. H. J. Cristau, B. Chabaud, A. Chêne, and H. Christol, Synthesis, 1981, 892.
24. C. Schultz, A. Link, M. Leost, D. W. Zaharevitz, R. Gussio, E. A. Sausville, L. Meijer, and C. Kunick, J. Med. Chem., 1999, 42, 2909.
25. 2O, rt) in high yields.
26. D. W. Brown, P. R. Graupner, M. Sainsbury, and H. G. Shertzer, Tetrahedron, 1991, 47, 4383.