The first syntheses of antiviral, cytotoxic 6-cyano-5-methoxy- and-12-methyundolo[2,3-a]carbazoles, and related indolo[2,3-a]carbazoles from indigo

Heterocycles

Volumn 45, Issue 9, 1997, Pages 1647-1650

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

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001079835     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-7848     Document Type: Article

References (13)

1. This is Part 84 of a series entitled "The Chemistry of Indoles". Part 83: F. Yamada, T. Hashizume, and M. Somei, Heterocycles, 1998, 47 (No. 1), in press All new compounds gave satisfactory spectral data and elemental analyses, la: mp >300°C; 1b: mp 299-301°C; 1 c: mp 200-201°C; 4 b: mp 233-235°C; 6a: mp 236-238°C (decomp); 6b: mp 263-264°C (decomp); 7: mp >300°C; 8a: mp 166-167°C; 8b: mp 246-252°C; 9a: mp >300°C; 9b: mp >300°C; 11a: mp244-245°C (decomp); lib: mp 236-237°C (decomp); 12: mp >300°C; 13: mp >300°C; 14: mp 62-64°C; 15: mp 240-245°C.
2. a) A. Fukusai, N. Hashiba, T. Matsumoto, A. Hirano, T. Iwai, and S. Omura, J. Chem. Soc., Chem. Commun., 1978, 800;
3. b) R. Bonjouklian, T. A. Smikta, L. E. Doolin, R. M. Moody, M. Debono, S. A. Shaffer, R. E. Moore, J. B. Stewart, and G. M. L. Patterson, Tetrahedron, 1991, 47, 7739;
4. c) K. Kojiri, H. Kondo, T. Yoshinari, H. Arakawa, S. Nakajima, F. Sato, K. Kawamura, A. Okura, H. Suda, and M. Okanish, J. Antibiotics, 1991, 44, 723;
5. M. Ohkubo, H. Kawamoto, T. Ohno, M. Nakano, and H. Morishima, Tetrahedron, 1997, 53, 585 and references cited therein.
6. G. Knubel, L. K. Larsen, R. E. Moore, I. A. Levine, and G. M. L. Patterson, J. Antibiotics, 1990, 43, 1236.
7. M. Somei, H. Hayashi, and S. Ohmoto, Heterocycles, 1997, 44, 169;
8. M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, Heterocycles, ibid., 1995, 41, 2161;
9. M. Somei and A. Kodama, Heterocycles, ibid., 1992, 34, 1285.
10. Definition of originality rate in English: M. Somei, Yakugaku Zasshi, 1988,108, 361;
11. in Japanese, J. Synth. Org. Chem., 1982, 40, 387.
12. a) Vice and co-workers reported the unstable 5-hydroxy derivative of indolo[2,3-a]carbazole: S. W. McCombie and S. F. Vice, J. Org. Chem., 1996, 61, 413;
13. b) Related 5,6-dibromo derivative is known: B. B. Shankar, S. W. McCombie, M. P. Kirkup, A. Q. Vict, M. S. Puar, and A. K. Ganguly, Tetrahedron Lett., 1993, 34, 5685.