Reduction of indigo: Simple syntheses of 3-acetoxy-, 1-acetyl-2.3-dihydro-, 3-acetoxy-3′-acetyl-, 3-acetoxy-1,3′-diacetyl-2,2′-bisindoles, and 2,2′-bisindole

Heterocycles

Volumn 44, Issue 1, 1997, Pages 169-176

  Somei, Masanori ^a   Hayashi, Hiroyuki ^a   Ohmoto, Shinobu ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001187179     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S4     Document Type: Article

References (13)

1. a) Dedicated to the 77th birthday of Dr. Shigeru Oae.
2. b) This is Part 77 of a series entitled "The Chemistry of Indoles". Part 76: M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, Heterocycles, 1995, 41, 2161.
3. Review: P. E. McGovem and R. H. Michel, Acc. Chem. Res., 1990, 23, 152 and references cited therein.
4. Reduction of indigo: J. Bergman and N. Eklund, Chemica Scripta, 1982, 19, 193;
5. W. Madelung and P. Siegert, Ber., 1924, 57, 222. See also references 2 and 4.
6. a) J. Bergman and N. Eklund, Tetrahedron, 1980, 36, 1439
7. tBu: J. Bergman, E. Koch, and B. Pelcman, Tetrahedron, 1995, 51, 5631 and references cited therein..
8. M. Somei and A. Kodama, Heterocycles, 1992, 34, 1285. See also reference 1b.
9. a) J. F. Barry, T. W. Wallace, and N. D. A. Walshe, Tetrahedron Lett., 1993, 34, 5329
10. b) U. Pindur, Y. -S. Kim, and D. Schollmeyer, J. Heterocycl. Chem., 1994, 31, 377;
11. c) U. Pindur, Y. -S. Kim, and D. Schollmeyer, Heterocycles, 1994, 38, 2267.
12. M. Somei, F. Yamada, H. Hamada, and T. Kawasaki, Heterocycles, 1989, 29, 643 and references cited therein.
13. The compound(5) and its derivatives were found to have potent biological activity: S. Sasaki, Y. Shoubu, T. Mizushima, K. Sekimizu, and M. Maeda, Abstract of Papers, No. 2, 115th Annual Meeting of Pharmaceutical Society of Japan, Sendai, March 1995, p. 270.