Synthetic entries to 6-fluoro-7-substituted indole derivatives

Autor: R. Noureldin, Andre A. Asselin, Robert John Steffan, Richard M. Soll, G. Gavin, Jean Schmid, Amedeo Arturo Failli, Brian Mckittrick, Philip F. Hughes, C. C. Shaw
Rok vydání: 1990
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 27:2151-2163
ISSN: 1943-5193
0022-152X
Popis: Three practical synthetic entries of functionalized 6-fluoro-7-substituted indole derivatives were developed in connection with the preparation of 7-fluoro-8-substituted-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid derivatives 11. The first route, which permits group modification about position 8 of the pyranoindole skeleton, employs 2-bromo-3-fluoroaniline (18) as a key intermediate, the preparation of which was achieved by either a novel ortho metalation of 15 or via the intermediacy of 22. The second route utilizes 32 to append a terminally functionalized three carbon side chain onto the indole template and in addition leads to 43 from 40. The third route to the 7-fluoro-8-substituted-pyranoindole skeleton complements route two in that the synthetic pathway exploits 32 in a nucleophilic fashion to construct a terminally functionalized two carbon appendage onto the indole nucleus.
Databáze: OpenAIRE
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