Acid-promoted competing pathways in the oxidative polymerization of 5,6- dihydroxyindoles and related compounds: Straightforward cyclotrimerization routes to diindolocarbazole derivatives

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 7002-7008

  Manini, Paola ^a   D'Ischia, Marco ^a   Milosa, Mario ^a   Prota, Giuseppe ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; OXIDATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032476125     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980875k     Document Type: Article

References (33)

1. Waring, D. R. In Comprehensive Heterocyclic Chemistry; Katritsky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 1, pp 317-318.
2. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970; pp 341-392.
3. (a) Auclair, C.; Vosin, E.; Banoun, H.; Paoletti, C.; Bernadou, J.; Meunier, B. J. Med. Chem. 1984, 27, 1161-1166.
4. (b) Kansal, V. K.; Funakoshi, S.; Mangeney, P.; Gillet, B.; Guittet, E.; Lallemand, J. Y.; Potier, P. Tetrahedron 1985, 41, 5107-5120.
5. (c) Kansal, V. K.; Sundaramoorthi, R.; Das, B. C.; Potier, P. Tetrahedron Lett. 1985, 26, 4933-4936.
6. (a) Bell, M. R.; Johnson, J. R.; Wildi, B. S.; Woodward, R. B. J. Am. Chem. Soc. 1958, 80, 1001.
7. (b) Stapleford, K. S. J. In Rodd's Chemistry of Carbon Compounds; Coffey, S., Ed.; Elsevier: Amsterdam, 1977; Vol. 4B, pp 63-163.
8. (c) McIntire, W. S.; Wemer, D. E.; Christoserdov, A.; Lidstrom, M. E. Science 1991, 252, 817-824.
9. (a) Prota, G. Melanins and Melanogenesis; Academic Press: San Diego, 1992.
10. (b) Prota, G. Fortschr. Chem. Organ. Naturst. 1995, 64, 93-148.
11. Napolitano, A.; Corradini, M. G.; Prota, G. Tetrahedron Lett. 1985, 26, 2805-2808.
12. For a recent review, see: (a) d'Ischia, M.; Napolitano, A.; Prota, G. Gazz. Chim. Ital. 1996, 126, 783-789. Other leading references: (b) Corradini, M. G.; Napolitano, A.; Prota, G. Tetrahedron 1986, 42, 2083-2088. (c) d'Ischia, M.; Napolitano, A.; Tsiakas, K.; Prota, G. Tetrahedron 1990, 46, 5789-5796.
13. For a recent review, see: (a) d'Ischia, M.; Napolitano, A.; Prota, G. Gazz. Chim. Ital. 1996, 126, 783-789. Other leading references: (b) Corradini, M. G.; Napolitano, A.; Prota, G. Tetrahedron 1986, 42, 2083-2088. (c) d'Ischia, M.; Napolitano, A.; Tsiakas, K.; Prota, G. Tetrahedron 1990, 46, 5789-5796.
14. For a recent review, see: (a) d'Ischia, M.; Napolitano, A.; Prota, G. Gazz. Chim. Ital. 1996, 126, 783-789. Other leading references: (b) Corradini, M. G.; Napolitano, A.; Prota, G. Tetrahedron 1986, 42, 2083-2088. (c) d'Ischia, M.; Napolitano, A.; Tsiakas, K.; Prota, G. Tetrahedron 1990, 46, 5789-5796.
15. (a) Napolitano, A.; d'Ischia, M.; Prota, G. Tetrahedron 1988, 44, 7265-7270.
16. (b) Napolitano, A.; d'Ischia, M.; Prota, G.; Schultz, T. M.; Wolfram, L. J. Tetrahedron 1989, 45, 6749-6760.
17. Minisci, F.; Citterio, A. Acc. Chem. Res. 1983, 16, 27-32.
18. For nomenclature and numbering system of diindolocarbazoles, see: Kaneko, T.; Matsuo, M.; Iitaka, Y. Chem. Pharm. Bull. 1981, 29, 3499-3506.
19. Napolitano, A.; Pezzella, A.; d'Ischia, M.; Prota, G. Tetrahedron Lett. 1996, 37, 4241-4242.
20. Remers, W. A.; Brown, R. K, In Indoles; Houlihan, W. J., Ed.; Wiley-Interscience: New York, 1972; Part I, pp 145-152.
21. Murphy, B. P.; Schultz, T. M. J. Org. Chem. 1985, 50, 2790-2791.
22. Napolitano, A.; Crescenzi, O.; Tsiakas, K.; Prota, G. Tetrahedron 1993, 49, 9143-9150.
23. Remers, W. A.; Brown, R. K. In Indoles; Houlihan, W. J., Ed.; Wiley-Interscience: New York, 1972; Part I, pp 66-70.
24. (a) Bergman, J.; Eklund, N. Tetrahedron 1980, 36, 1445-1450.
25. (b) Bergman, J.; Eklund, N. Tetrahedron 1980, 36, 1439-1443.
26. (c) Bocchi, V.; Palla, G. Tetrahedron 1986, 42, 5019-5024.
27. (d) Eissenstat, M. A.; Bell, M. R.; D'Ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V.; Estep, K. G.; Olefirowicz, E. M.; Wetzel, J. R.; Alexander, M. D.; Weaver, J. D.; Haycock, D. A.; Luttinger, D. A.; Casiano, F. M.; Chippari, S. M.; Kuster, J. E.; Stevenson, J. I.; Ward, S. J. J. Med. Chem. 1995, 16, 3094-3105.
28. Benigni, J. D.; Minnis, R. L. J. Heterocycl. Chem. 1965, 2, 387-392.
29. Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91-95.
30. 13C NMR spectrum, whereas a poor spectrum was obtained in the case of 6b even after a high number of scans.
31. 1H NMR spectrum (400 MHz) is provided as Supporting Information.
32. Neil, A. B. J. Am. Chem. Soc. 1953, 75, 1508.
33. Witkop, B.; Patrick, J. B. J. Am. Chem. Soc. 1951, 73, 713-718.