A synthetic use of the intramolecular alkyl migration process in indolylborates for intramolecular cyclization: A novel construction of carbazole derivatives

Tetrahedron

Volumn 58, Issue 49, 2002, Pages 9827-9838

  Ishikura, Minoru ^a   Kato, Hiromi ^a  

^a HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

Carbazoles; Indolylborate; Intramolecular alkyl migration; Palladium catalyst

Indexed keywords

BORIC ACID; CARBAZOLE DERIVATIVE; INDOLE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037010792     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01293-0     Document Type: Article

References (25)

1. (a) Sundberg R.J. The Chemistry of Indoles. 1970;Academic, London
2. (b) Sundberg R.J. Indoles. 1996;Academic, San Diego.
3. (a) Ishikura M., Agata I. Recent Res. Dev. Org. Chem. 1:1997;145-157
4. (b) Ishikura M. Curr. Org. Chem. 6:2002;507-521.
5. (a) Ishikura M., Hino A., Yaginuma T., Agata I., Katagiri N. Tetrahedron. 56:2000;193-207
6. (b) Ishikura M., Imaizumi K., Katagiri N. Heterocycles. 53:2000;2201-2220.
7. (a) Brown H.C. Organic Synthesis via Boranes. 1975;Wiley, New York
8. (b) Mikhailov B.M., Bubnov Y.N. Organoboron Compounds in Organic Synthesis. 1983;Harwood Academic, London
9. (c) Negishi E., Idacavage M.J. Org. React. 33:1985;1-246.
10. (a) Levy A.B. J. Org. Chem. 43:1978;4684-4685
11. (b) Marinelli E.R., Levy A.B. Tetrahedron Lett. 1979;2313-2316
12. (c) Sotoyama T., Hara S., Suzuki A. Bull. Chem. Soc. Jpn. 52:1979;1865-1866
13. (d) Ishikura M., Ohta T., Terashima M. Heterocycles. 24:1986;2793-2796
14. (e) Terashima M., Ishikura M. Adv. Heterocycl. Chem. 46:1989;143-167.
15. Ishikura M., Terashima M., Okamura K., Date T. J. Chem. Soc., Chem. Commun. 1991;1219-1221.
16. Ishikura M., Matsuzaki Y., Agata I., Katagiri N. Tetrahedron. 54:1998;13929-13942.
17. Ishikura M., Agata I., Katagiri N. J. Heterocycl. Chem. 36:1999;873-879.
18. Hwa C.H., Sims H. Organic Synthesis. Coll. Vol. 5:1973;Wiley, New York. pp 608-612.
19. Ishikura M., Kato H., Ohnuki N. Chem. Commun. 2002;220-221.
20. Conflone P.N., Baggiolini E., Hennessy B., Uskokovic M.R. J. Org. Chem. 46:1981;4923-4927.
21. Stork G., Danheiser R.L. J. Org. Chem. 38:1973;1775-1776.
22. (a) Takahashi K., Jinbo Y., Kitamura K., Tsuji J. Tetrahedron Lett. 25:1984;5921-5924
23. (b) Ogoshi S., Kurosawa H. Chem. Lett. 1990;1745-1748
24. (c) Kurosawa H., Ogoshi S., Chatani N., Kawasaki Y. Organometallics. 12:1993;2869-2871
25. (d) Granberg K.L., Bäckvall J.E. J. Am. Chem. Soc. 114:1992;6858-6863.