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Convergent synthesis of 6-substituted phenanthridines via anionic ring closure

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Chemical equation presented The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 °C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature. The addition of the corresponding Grignard reagents requires an excess of the organometallic reagent and extented reaction times at elevated temperature.
OriginalsprogEngelsk
TidsskriftOrganic Letters
Vol/bind4
Udgave nummer2
Sider (fra-til)257-259
Antal sider3
ISSN1523-7060
DOI
StatusUdgivet - 1 jan. 2002

ID: 45438116