Modifications to the Vilsmeier-Haack formylation of 1,4-dimethylcarbazole and its application to the synthesis of ellipticines

Journal of Heterocyclic Chemistry

Volumn 48, Issue 4, 2011, Pages 814-823

  Deane, Fiona M ^a   Miller, Charlotte M ^a   Maguire, Anita R ^a   McCarthy, Florence O ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIMETHYLCARBAZOLE; 1,4,9 TRIMETHYLCARBAZOLE; 3 FORMYL 1,4 DIMETHYLCARBAZOLE; 3 FORMYL 1,4,9 TRIMETHYLCARBAZOLE; 3 FORMYL 6 METHOXY 1,4 DIMETHYLCARBAZOLE; 6 FORMYL 1,4 DIMETHYLCARBAZOLE; 6 FORMYL 1,4,9 TRIMETHYLCARBAZOLE; 6 METHOXY 1,4 DIMETHYLCARBAZOLE; 6 METHYLELLIPTICINE; 6 METHYLELLIPTICINE (5,6,11 TRIMETHYL 6H PYRIDO[4,3 B]CARBAZOLE); 7 FORMYL 6 METHOXY 1,4 DIMETHYLCARBAZOLE; 8 FORMYL 6 METHOXY 1,4 DIMETHYLCARBAZOLE; 9 FORMYL 1,4 DIMETHYLCARBAZOLE; 9 METHOXYELLIPTICINE; CARBAZOLE DERIVATIVE; ELLIPTICINE DERIVATIVE; ELLIPTINIUM ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; FORMYLATION; VILSMEIER HAACK REACTION;

EID: 79960841561     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.598     Document Type: Article

References (19)

1. Garbett, N. C.; Graves, D. E., Curr Med Chem Anticancer Agents 2004, 4, 149.
2. Stiborová, M.; Bieler, C. A.; Wiessler, M.; Frei, E., Biochem Pharmacol 2001, 62, 1675.
3. Stiborová, M.; Breuer, A.; Aimová, D.; Stiborová- Rupertová, M.; Wiessler, M.; Frei, E., Int J Cancer 2003, 107, 885.
4. Auclair, C., Arch Biochem Biophys 1987, 259, 1.
5. Vendãme, J.; Letard, S.; Martin, F.; Svinarchuk, F.; Dubreuil, P.; Auclair, C.; Le Bret, M., J Med Chem 2005, 48, 6194.
6. Thompson, D.; Miller, C.; McCarthy, F. O., Biochemistry 2008, 47, 10333.
7. Hewlins, M. J. E.; Oliveira-Campos, A. M.; Shannon, P. V. R., Synthesis 1984, 4, 289.
8. Gribble, G. W.; Saulnier, M. G., Heterocycles 1985, 23, 1277.
9. Sainsbury, M., Synthesis 1977, 437.
10. Gribble, G. W., The Alkaloids 1990, 39, 239.
11. Cranwell, P. A.; Saxton, J. E., J Chem Soc 1962, 3482.
12. Dalton, L. K.; Demerac, S.; Elmes, B. C.; Loder, J. W.; Swan, J. M.; Teitei, T., Aust J Chem 1967, 20, 2715.
13. Guthrie, R. W.; Brossi, A.; Mennona, F. A.; Mullin, J. G.; Kierstead, R. W.; Grunberg, E., J Med Chem 1975, 18, 755.
14. Dracínskã, M.; Sejbal, J.; Rygerová, B.; Stiborová, M., Tetrahedron Lett 2007, 48, 6893.
15. Dalton, L. K.; Demerac, S.; Teitei, T., Aust J Chem 1969, 22, 185.
16. Jackson, A. H.; Jenkins, P. R.; Shannon, P.; V. R., J Chem Soc Perkin Trans 1 1977, 14, 1698.
17. Plug, J. P. M.; Koomen, G.-J.; Pandit, U. K., Synthesis 1992, 1221.
18. Yokoyama, Y.; Okuyama, N.; Iwadate, S.; Momoi, T.; Murakami, Y., J Chem Soc Perkin Trans 1 1990, 1319.
19. Sainsbury, M.; Smith, A. D.; Vong, K. K.; Scopes, D. I., J Chem Soc Perkin Trans 1 1988, 2945.