Synthesis of dibenzazepinones by palladium-catalyzed intramolecular arylation of o-(2'-bromophenyl)anilide enolates.
A new approach for the convenient synthesis of dibenzazepinones is reported. The key step is the formation of the seven-membered ring through palladium-catalyzed intramolecular arylation of an anilide enolate. The reactions were completed in 10 min at 100 °C with moderate to excellent yields. Aminodibenzazepinone 1, the core structure in the γ-secretase inhibitor LY411575, can be prepared in five steps from 2-bromophenylboronic acid and 2-iodoaniline in 60% overall yield. The synthesis reported here compares favorably with presently available approaches to this interesting ring system.
Pan
Xiaohong
X
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Wilcox
Craig S
CS
D000813:Anilides / Q000737:chemistry*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000813:Anilides; D001552:Benzazepines; D007659:Ketones; D009942:Organometallic Compounds; D010165:Palladium