The synthesis of naphtho[a]carbazoles and benzo[c]carbazoles

Synlett

Volumn , Issue 5, 2003, Pages 705-707

  De Koning, Charles B ^a   Michael, Joseph P ^a   Nhlapo, Johanna M ^a   Pathak, Rakhi ^a   Van Otterlo, Willem A L ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Benzo c carbazoles; Carbazoles; Indoles; Naphtho a carbazoles; Suzuki coupling

Indexed keywords

1 METHYL 2 (2 METHYL 1 NAPHTHYL) 1H INDOLE 3 CARBALDEHYDE; 11 METHYL 11H NAPHTHOL[2,1 A]CARBAZOLE; CARBAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON; METHODOLOGY; METHYLATION; SYNTHESIS;

EID: 0037263649     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38352     Document Type: Article

References (21)

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10. Carini, D. J.; Kaltenbach, R. F. III.; Liu, J.; Benfield, P. A.; Boylan, J.; Boisclair, M.; Brizuela, L.; Burton, C. R.; Cox, S.; Grafstrom, R.; Harrison, B. A.; Harrison, K.; Akamike, E.; Markwalder, J. A.; Nakano, Y.; Seitz, S. P.; Sharp, D. M.; Trainor, G. L.; Sielecki, T. M. Bioorg. Med. Chem. Lett. 2001, 11, 2209.
11. de Koning, C. B.; Michael, J. P.; Rousseau, A. L. Tetrahedron Lett. 1998, 39, 8725.
12. de Koning, C. B.; Michael, J. P.; Rousseau, A. L. J. Chem. Soc., Perkin Trans. 1 2000, 1705.
13. 3, 6.69 mmol) was added. An off-white crystalline material, 1-methyl-2-naphthylboronic acid 5b (0.39 g, 93%) was produced, which was used without further purification or characterization. (d) Parham, W. E.; Reiff, H. E.; Swartzentruber, P. J. Am. Chem. Soc. 1956, 78, 1437. (e) 1,4-Dimethoxy-3-methyl-2-naphthylboronic Acid 5c. 2-Bromo-1,4-dimethoxy-3-methylnaphthalene was prepared according to: Adams, R.; Geissman, T. A.; Baker, B. R.; Teeter, H. M. J. Am. Chem. Soc. 1941, 63, 528; this was then treated as described above to afford the desired boronic acid 5c..
14. 3, 6.69 mmol) was added. An off-white crystalline material, 1-methyl-2-naphthylboronic acid 5b (0.39 g, 93%) was produced, which was used without further purification or characterization. (d) Parham, W. E.; Reiff, H. E.; Swartzentruber, P. J. Am. Chem. Soc. 1956, 78, 1437. (e) 1,4-Dimethoxy-3-methyl-2-naphthylboronic Acid 5c. 2-Bromo-1,4-dimethoxy-3-methylnaphthalene was prepared according to: Adams, R.; Geissman, T. A.; Baker, B. R.; Teeter, H. M. J. Am. Chem. Soc. 1941, 63, 528; this was then treated as described above to afford the desired boronic acid 5c..
15. 3, 6.69 mmol) was added. An off-white crystalline material, 1-methyl-2-naphthylboronic acid 5b (0.39 g, 93%) was produced, which was used without further purification or characterization. (d) Parham, W. E.; Reiff, H. E.; Swartzentruber, P. J. Am. Chem. Soc. 1956, 78, 1437. (e) 1,4-Dimethoxy-3-methyl-2-naphthylboronic Acid 5c. 2-Bromo-1,4-dimethoxy-3-methylnaphthalene was prepared according to: Adams, R.; Geissman, T. A.; Baker, B. R.; Teeter, H. M. J. Am. Chem. Soc. 1941, 63, 528; this was then treated as described above to afford the desired boronic acid 5c..
16. 3, 6.69 mmol) was added. An off-white crystalline material, 1-methyl-2-naphthylboronic acid 5b (0.39 g, 93%) was produced, which was used without further purification or characterization. (d) Parham, W. E.; Reiff, H. E.; Swartzentruber, P. J. Am. Chem. Soc. 1956, 78, 1437. (e) 1,4-Dimethoxy-3-methyl-2-naphthylboronic Acid 5c. 2-Bromo-1,4-dimethoxy-3-methylnaphthalene was prepared according to: Adams, R.; Geissman, T. A.; Baker, B. R.; Teeter, H. M. J. Am. Chem. Soc. 1941, 63, 528; this was then treated as described above to afford the desired boronic acid 5c..
17. 3, 6.69 mmol) was added. An off-white crystalline material, 1-methyl-2-naphthylboronic acid 5b (0.39 g, 93%) was produced, which was used without further purification or characterization. (d) Parham, W. E.; Reiff, H. E.; Swartzentruber, P. J. Am. Chem. Soc. 1956, 78, 1437. (e) 1,4-Dimethoxy-3-methyl-2-naphthylboronic Acid 5c. 2-Bromo-1,4-dimethoxy-3-methylnaphthalene was prepared according to: Adams, R.; Geissman, T. A.; Baker, B. R.; Teeter, H. M. J. Am. Chem. Soc. 1941, 63, 528; this was then treated as described above to afford the desired boronic acid 5c..
18. +], 284 (38), 282 (55), 254 (19), 127.
19. +], 266 (22), 252 (3), 140(2).
20. This work is taken from the PhD of R. Pathak.
21. This work is taken from the MSc of J. M. Nhlapo.