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 |
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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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