Synthesis of imidazolo[5,4-b]carbazole-4,10-quinones

Synlett

Volumn , Issue 7, 2004, Pages 1306-1308

  Desforges, Gwénaëlle ^a   Bossert, Cécile ^a   Montagne, Cyril ^a   Joseph, Benoît ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Ellipticine; Imidazole; Metalation; Quinone

Indexed keywords

CARBAZOLE DERIVATIVE; CARBONYL DERIVATIVE; CARBOQUONE; CARBOXYLIC ACID DERIVATIVE; ELLIPTICINE DERIVATIVE; HALOGEN; IMIDAZOLE; METAL; QUINONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; GRIGNARD REACTION; PROTON TRANSPORT; REACTION OPTIMIZATION; SYNTHESIS;

EID: 2942708137     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822923     Document Type: Article

References (19)

1. Furukawa, H.; Wu, T.-S.; Ohta, T.; Kuoh, C.-S. Chem. Pharm. Bull. 1985, 33, 4132.
2. Rickards, R. W.; Rothschild, J. M.; Willis, A. C.; de Chazal, N. M.; Kirk, K.; Saliba, K. J.; Smith, G. D. Tetrahedron 1999, 55, 13513.
3. Saha, C.; Chowdhury, B. K. Phytochemistry 1998, 48, 363.
4. Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Lee, K.-H. Bioorg. Med. Chem. Lett. 1994, 4, 2395.
5. Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1983, 48, 2690.
6. Bergman, J.; Wahlström, N.; Yudina, L. N.; Tholander, J.; Lidgren, G. Tetrahedron 2002, 58, 1443.
7. Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
8. Knölker, H.-J.; Reddy, K. R. Heterocycles 2003, 60, 1049.
9. (a) Poumaroux, A.; Bouaziz, Z.; Fillion, H.; Domard, M.; Giraud, J.; Pétavy, A.-F. Chem. Pharm. Bull. 1999, 47, 643.
10. (b) Bouaziz, Z.; Ghérardi, A.; Régnier, F.; Sarciron, M.-E.; Bertheau, X.; Fenet, B.; Walchshofer, N.; Fillion, H. Eur. J. Org. Chem. 2002, 1834.
11. Bernardo, P. H.; Chai, C. L. L.; Elix, J. A. Tetrahedron Lett. 2002, 42, 2939.
12. Kelly, T. R.; Zhao, Y.; Cavero, M.; Torneiro, M. Org. Lett. 2000, 2, 3735.
13. Iddon, B.; Lim, B. L. J. Chem. Soc., Perkin Trans. 1 1983, 735.
14. Butz, R. H.-J.; Lindell, S. D. J. Org. Chem. 2002, 67, 2699.
15. Abarbri, M.; Thibonnet, J.; Bérillon, L.; Dehmel, F.; Rottländer, M.; Knochel, P. J. Org. Chem. 2000, 65, 4618.
16. Using standard conditions (esterification, Vilsmeier-Haack formylation, N-Boc-protection) the indole derivative 4 was prepared from commercially available indole-2-carboxylic acid in 94% overall yield.
17. 3: 330.0645; found: 330.0645.
18. 13C NMR (except carbonyl signals), IR, MS and HRMS.
19. Kuo, S.-C.; Ibuka, T.; Huang, L.-J.; Lien, J.-C.; Yean, S.-R.; Huang, S.-C.; Lednicer, D.; Morris-Natschke, S.; Lee, K.-H. J. Med. Chem. 1996, 36, 1447.