Short step syntheses of a natural product, 6-cyano-5-methoxy-12- methylindolo[2,3-a]carbazole and novel 6-aminoindolo[2,3-a]-thiazolo[5,4- c]carbazoles

Heterocycles

Volumn 51, Issue 6, 1999, Pages 1233-1235

  Hayashi, Hiroyuki ^a   Suzuki, Yoshiaki ^a   Somei, Masanori ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINOINDOLO[2,3 A]THIAZOLO[5,4 C]CARBAZOLE; 6 CYANO 5 METHOXY 12 METHYLINDOLO[2,3 A]CARBAZOLE; CARBAZOLE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0033150520     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-8531     Document Type: Article

References (14)

1. This is Part 90 of a series entitled "The Chemistry of Indoles". Part 89: K. Yamada and M. Somei, Heterocycles, 1998, 48, 2481. All new compounds gave satisfactory spectral data and elemental analyses. 4: mp 227-229°C (decomp); 5a: mp 236-238°C (decomp); 5b: mp 223-225°C (decomp); 6a: mp > 300°C; 8a mp 238-241°C (decomp); 8b: mp 240°C (decomp); 9a mp 140-141°C; 9b: mp >300°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. Okanishi, J. Antibiotics, 1991, 44, 723; M. Ohkubo, H. Kawamoto, T. Ohno, M. Nakano, and H. Morishima, Tetrahedron, 1997, 53, 585 and references cited therein.
5. c) K. Kojiri, H. Kondo, T. Yoshinari, H. Arakawa, S. Nakajima, F. Sato, K. Kawamura, A. Okura, H. Suda, and M. Okanishi, J. Antibiotics, 1991, 44, 723; M. Ohkubo, H. Kawamoto, T. Ohno, M. Nakano, and H. Morishima, Tetrahedron, 1997, 53, 585 and references cited therein.
6. G. Knübel, L. K. Larsen, R. E. Moore, I. A. Levine, and G. M. L. Patterson, J. Antibiotics, 1990, 43, 1236.
7. H. Hayashi, S. Ohmoto, and M. Somei, Heterocycles, 1997, 45, 1647; M. Somei, H. Hayashi, and S. Ohmoto, ibid., 1997, 44, 169; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei and A. Kodama, ibid., 1992, 34, 1285.
8. H. Hayashi, S. Ohmoto, and M. Somei, Heterocycles, 1997, 45, 1647; M. Somei, H. Hayashi, and S. Ohmoto, ibid., 1997, 44, 169; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei and A. Kodama, ibid., 1992, 34, 1285.
9. H. Hayashi, S. Ohmoto, and M. Somei, Heterocycles, 1997, 45, 1647; M. Somei, H. Hayashi, and S. Ohmoto, ibid., 1997, 44, 169; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei and A. Kodama, ibid., 1992, 34, 1285.
10. H. Hayashi, S. Ohmoto, and M. Somei, Heterocycles, 1997, 45, 1647; M. Somei, H. Hayashi, and S. Ohmoto, ibid., 1997, 44, 169; M. Somei, H. Hayashi, T. Izumi, and S. Ohmoto, ibid., 1995, 41, 2161; M. Somei and A. Kodama, ibid., 1992, 34, 1285.
11. In the trans-isomer, both 6-chlorine atom and 6a-hydroxy group must exist in thermodynamically unstable axial positions. Furthermore, by the reaction with bases, 5a did not generate the corresponding epoxide. From these facts, cis-configuration of 5a is deduced.
12. Definition of originality rate in English: M. Somei, Yakugaku Zasshi, 1988, 108, 361; in Japanese, M. Somei, J. Synth. Org. Chem., 1982, 40, 387.
13. Definition of originality rate in English: M. Somei, Yakugaku Zasshi, 1988, 108, 361; in Japanese, M. Somei, J. Synth. Org. Chem., 1982, 40, 387.
14. Related indolo[2,3-a]oxazolo[4,5-c]carbazol-6-one and indolo[2,3-a]imidazolo[4,5-c]carbazol-6-one derivatives were reported: E. R. Pereira, M. Prudhomme, M. Sancelme, M. Oilier, D. Severe, J. F. Riou, H. Crevel, J. P. Savineau, D. Fabbro, and T. Meyer, Chem. Pharm. Bull., 1997, 45, 733 and references cited therein.