Halogen-magnesium exchange reaction of iodoindole derivatives

Heterocycles

Volumn 42, Issue 1, 1996, Pages 105-108

  Kondo, Yoshinori ^a   Yoshida, Akihiro ^a   Sato, Shuichiroh ^a   Sakamoto, Takao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001031256     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s31     Document Type: Article

References (16)

1. (a) B. J. Wakefield, "The Chemistry of Organolithium Compounds", Pergamon Press, Oxford, 1974.
2. (b) B. J. Wakefield, "Organolithium Method", Academic Press, London, 1988.
3. (c) G. W. Rewcastle and A. R. Katritzky, Adv. Heterocycl. Chem., 1993, 56, 155.
4. M. G. Saulnier and G. W. Gribble, J. Org. Chem., 1982, 47, 757.
5. M. Amat, S. Hadida, S. Sathyanarayana, and J. Bosch, J. Org. Chem., 1994, 59, 10.
6. (a) Y-H. Lai, Synthesis, 1981, 585.
7. (b) Magnesioindoles have not yet prepared via oxidative addition of metallic magnesium. We preliminarily examined oxidative addition of metallic magnesium (turnings) to the 3-iodoindole, however the reaction was sluggish and unsuccessful.
8. (a) H. H. Paradies and M. Gorbing, Angew. Chem., 1969, 81, 293.
9. (b) C. F. Smith, G. J. Moore, and C. Tamborski, J. Organomet. Chem., 1971, 33, C21.
10. (c) C. Tamborski and G. J. Moore, J. Organomet. Chem., 1971, 26, 153.
11. (a) T. Sakamoto, Y. Kondo, N. Takazawa, and H. Yamanaka, Heteroycles, 1993, 36, 941.
12. (b) T. Sakamoto, Y Kondo, N. Takazawa, and H. Yamanaka, Tetrahedron Lett., 1993, 34, 5955.
13. T. Sakamoto, Y Kondo, S. Sato, and H. Yamanaka, Tetrahedron Lett., 1994, 35, 2919.
14. (a) N. Tanaka, R.-T. Wu, T. Okabe, H. Yamashita, A. Shimazu, and T. Nishimura, J. Antibiotics, 1982, 35, 272.
15. (b) R.-T. Wu, T. Okabe, M. Namikoshi, S. Okuda, T. Nishimura, and N. Tanaka, J. Antibiotics, 1982, 35, 279.
16. 3) δ: 2.20-2.22 (1H, d, J=4.4 Hz), 6.02-6.03 (1H, d, J=3.3 Hz), 7.15-7.18 (1H, m), 7.26-7.56 (11H, m), 7.86-7.89 (2H, m), 7.96-7.99 (1H, d, J=8.42).