Some applications of the regioselective lithiation of α-carbolines

Heterocycles

Volumn 47, Issue 2, 1998, Pages 991-1004

  Papamicaël, Cyril ^a   Dupas, Georges ^a   Quéguiner, Guy ^a   Bourguignon, Jean ^a  

^a UNIVERSITÉ ET INSA DE ROUEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001132894     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)64     Document Type: Article

References (34)

1. A. A. Semenov and V. V. Tolstikhina, Khim. Geterosikl. Soedin., 1984, 4, 435;
2. N. Helbecque, C. Moquin, J. L. Bernier, E. Morel, M. Guyot, and J. P. Hénichart, Cancer Biochem. Biophys., 1987, 9, 271;
3. N. N. Pogodaeva, V. A. Shagun, and A. A. Semenov, Khim. Farm. Zh. SSSR, 1985, 19, 1054.
4. C. Moquin-Pattey and M. Guyot, Tetrahedron, 1989, 45, 3445 and references cited therein.
5. S. A. Abas, M. B. Hossain, D. van der Helm, and F. J. Schmitz, J. Org. Chem., 1996, 61, 2709.
6. a) S. Achab, M. Guyot, and P. Potier, Tetrahedron Lett., 1993, 34, 2127.
7. b) S. Achab, M. Guyot, and P. Potier, Tetrahedron Lett., 1995, 36, 2615.
8. a) T. Choshi, S. Yamada, E. Sugino, T. Kuwada, and S. Hibino, Syn. Lett., 1995, 147.
9. b) T. Choshi, S. Yamada, E. Sugino, T. Kuwada, and S. Hibino, J. Org. Chem., 1995, 60, 5899.
10. C. Papamicaël, G. Dupas, J. Bourguignon, and G. Quéguiner, Tetrahedron Lett., 1994, 35, 4099.
11. T. Watanabe, N. Miyaura, and A. Suzuki, Syn. Lett., 1992, 207.
12. V. Levacher, N. Boussad, G. Dupas, J. Bourguignon, and G. Qúguiner, Tetrahedron, 1992, 48, 831.
13. J Becher, K. Pluta, N. Krabe, K. Brondum, N. J. Christensen, and M. V. Vinader, Synthesis, 1989, 530.
14. M. J. Tanga, J. E. Bupp, and T. K. Tochimoto, J. Heterocycl. Chem., 1994, 31, 1641.Méthode BrCN
15. F. Suzuki, T. Kuroda, Y. Nakasato, H. Manabe, K. Ohmori, S. Kitamura, J. Med. Chem., 1992, 35, 4045.
16. H. G. Viehe and Z. Janousek, Angew. Chem., Int. Ed. Engl., 1973, 12, 806.
17. R. Benhida, T. Gharbaoui, A. Lechevallier, and R. Beugelmans, Bull. Soc. Chim. Fr., 1994, 131, 200;
18. T. Gharbaoui, R. Benhida, J. Chastanet, A. Lechevallier, P. Maillos, and R. Beugelmans, Bull. Soc. Chim. Fr., 1994, 131, 561;
19. R. Beugelmans, A. Lechevallier, R. Benhida, T. Gharbaoui, and A. Morris, Heterocycles, 1994, 38, 2199;
20. R. M. Claramunt, J. Dotor, D. Sanz, C. Foces-Foces, A. L. Llamas-Saiz, J. Elguero, R. Flammang, J. P. Morizur, E. Chapon, and J. Tortajada, Helv. Chim. Acta, 1994, 77, 121.
21. P. Barraclough, J. C. Lindon, M. S. Nobbs, and J. M. Williams, Magn. Res. Chem., 1989, 27, 992;
22. A. V. Tretyakov, L. I. Rudaya, A. V. El'tsov, M. F. Larin, and V. A. Lopyrev, Magn. Res. Chem., 1985, 23, 7.
23. R. M. Roberts and M. B. Edwards, J. Am. Chem. Soc., 1950, 72, 5537;
24. J. Davoll, J. Chem. Soc., 1960, 308;
25. M. Israel, L. C. Jones, and E. J. Modest, Tetrahedron Lett., 1968, 4811;
26. R. Achour, E. M. Essassi, and R. Zniber, Tetrahedron Lett., 1988, 195;
27. D. M. Raho, T. Giridhar, G. V. Prasad, R. B. Reddy, and G. V. P. C. Mouli, Heterocycles, 1997, 45, 19.
28. For a review see S. H. Pine, 'Organic Reactions: The Base-promoted Rearrangements of Quaternary Ammonium Salts', Vol. 18, ed. by W. G. Dauben, John Wiley and Sons, New York, 1970, pp. 403-464.
29. For recent synthetic applications see F. G. West and B. N. Naidu, J. Am. Chem. Soc., 1993, 115, 1177;
30. F. G. West and B. N. Naidu, J. Org. Chem., 1994, 59, 6051.
31. For a theoritical study see G. L. Heard and B. F. Yates, J. Org. Chem., 1996, 61, 7276.
32. E. Carceller, M. Merlos, M. Giral, D. Balsa, J. Garcia-Rafanell, and J. Forn, J. Med. Chem, 1996, 39, 487.
33. Some authors find better to prepare phosgene iminium chloride. See for example: M. Vilkas and D. Qasmi, Syn. Commun., 1990, 20, 2769.
34. F. Marsais, J. C. Rovera, A. Turck, A. Godard, and G. Quéguiner, J. Chem. Soc., Perkin Trans, 1, 1990, 2611.