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.
Original languageEnglish
JournalOrganic Letters
Issue number2
Pages (from-to)257-259
Number of pages3
Publication statusPublished - 1 Jan 2002

ID: 45438116