Synthesis of 4-(2-aminoethyl)indoles through claisen orthoamide rearrangement of 3-hydroxy-2-methoxyindolines

Heterocycles

Volumn 47, Issue 1, 1998, Pages 367-373

  Kawasaki, Tomomi ^a   Ohtsuka, Hiroaki ^a   Mihira, Ado ^a   Sakamoto, Masanori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1642345242     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s(n)32     Document Type: Article

References (33)

1. P. A. Stadler and P. Stütz, "The Ergot Alkaloids" in "The Alkaloids", Vol. 15, ed. by R. H. F. Manske, Academic Press, 1975, p 1.
2. H. Sato, H. Kawagishi, T. Nishimura, S. Yoneyama, Y Yoshimoto, S. Sakamura, A. Furusaki, S. Katsuragi, and T. Matsumoto, Agric. Biol. Chem., 1985, 49, 2969.
3. H. Wikstrom, B. Andersson, A. Svensson, L. G. Humber, A. A. Asselin, K. Svensson, A. Ekman, A. Carlsson, I. Nilsson, and C. Chidester, J. Med. Chem., 1989, 32, 2273.
4. J. G. Cannon, B. J. Demopoulos, J. P. Long, J. R. Flynn, and F. M. Sharabi, J. Med. Chem., 1981, 24, 238;
5. J. G. Cannon, T. Lee, M. Ilhan, J. Koons, and J. P. Long, J. Med. Chem., ibid., 1984, 27, 386.
6. H. G. Floss, Tetrahedron, 1976, 32, 873.
7. P. J. Beswick, C. S. Greenwood, T. J. Mowlem, G. Nechvatal, and D. A. Widdowson, Tetrahedron, 1988, 44, 7325, and references therein;
8. M. F. Semmelhack, P. Knochel, and T. Singleton, Tetrahedron Lett., 1993, 34, 5051.
9. M. Somei, Yakugaku Zasshi, 1988, 108, 361;
10. J. P. Konopelski, J. M.Hottenroth, H. M. Oltra, E. A. Véliz, and Z.-C. Yang, Synlett, 1996, 609.
11. M. Iwao, Heterocycles, 1993, 36, 29;
12. M. Iwao and F. Ishibashi, Tetrahedron, 1997, 53, 51.
13. P. A. Kozikowski, Heterocycles, 1981, 16, 267;
14. D. C. Horwell, Tetrahedron, 1980, 36, 3123.
15. E. Reimann and E. Hargasser, Arch. Pharm., 1988, 321, 823;
16. S. Nakatsuka, K. Yamada, and T. Goto, Tetrahedron Lett., 1986, 27, 4757.
17. I. K. Stamos and H. K. Kotzamani, J. Heterocycl. Chem., 1995, 32, 947.
18. A. L. Beck, M. Mascal, C. J. Moody, A. M. Slawin, D. J. Williams, and W. J. Coates, J. Chem. Soc., Perkin Trans. 1, 1992, 797;
19. A. L. Beck, M. Mascal, C. J. Moody, and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, ibid., 1992, 813;
20. M. Mascal, C. J. Moody, A. I. Morrell, A. M. Slawin, and D. J. Williams, J. Am. Chem. Soc., 1993, 115, 813.
21. K. Teranishi, S. Hayashi, S. Nakatsuka, and T. Goto, Tetrahedron Lett., 1994, 35, 8173;
22. K. Teranishi, S. Hayashi, S. Nakatsuka, and T. Goto, idem, Synthesis, 1994, 506.
23. P. Wipf, "Claisen Rearrangement" in "Comprehensive Organic Synthesis", Vol. 5, ed. by B. M. Trost, Pergamon Press, Oxford, 1991, p. 827;
24. F. E. Zieglar, Chem. Rev., 1988, 88, 1423;
25. C. J. Moody, "Claisen Rearrangement in Heteroaromatic Systems" in "Advances in Heterocyclic Chemistry", Vol. 42, ed. by A. R. Katritzky, Academic Press, 1987, p 203;
26. S. J. Rhoads and N. R. Raulins, "The Claisen and Cope Rearrangement" in "Organic Reaction", Vol. 22, ed. by W. G. Dauben, John Wiley & Sons, New York, 1975, p 1.
27. M. Makosza, J. Stalewski, K. Wojciechowski, and W. Danikiewicz, Tetrahedron, 1997, 53, 193;
28. J. H. Hutchinson, E. J. McEachern, J. Scheigetz, D. Macdonald, and M. Thérien, Tetrahedron Lett., 1992, 33, 4713;
29. M. Julia and J.-Y. Lallemand, Bull. Soc. Chim. Fr., 1973, 2046.
30. T. Kawasaki, H. Ohtsuka, and M. Sakamoto, J. Chem. Soc., Chem. Commun., 1990, 781.
31. C.-S. Chien, T. Suzuki, T. Kawasaki, and M. Sakamoto, Chem. Pharm. Bull., 1984, 32, 3945;
32. C.-S. Chien, A. Hasegawa, T. Kawasaki, and M. Sakamoto, Chem. Pharm. Bull., ibid., 1986, 34, 1493.
33. H. Meerwein, W. Florian, N. Schon, and G. Stopp, Liebigs Ann. Chem., 1961, 641, 1.