Author/Authors :
Sakya، نويسنده , , Subas M. and Flick، نويسنده , , Andrew C. and Coe، نويسنده , , Jotham W. and Gray، نويسنده , , David L. and Liang، نويسنده , , Sidney and Ferri، نويسنده , , Fabiola and Van Den Berg، نويسنده , , Michel and Pouwer، نويسنده , , Kees، نويسنده ,
Abstract :
Two syntheses of versatile intermediate azepinones 2 and 3 are described. A 6-step intramolecular Dieckmann cyclization and decarboxylation led to the intermediate 3 while an alternate 4-step synthesis of 2 was developed and used for scale-up. The highlight of the second synthesis is the one-step per-bromination/elimination protocol from readily available azepinone 13a to provide a versatile scaffold in vinyl bromide 5, which enables SAR around the aryl moiety. An example of the elaboration of the intermediate 2 toward a heteroaryl azepinone is also described.
Keywords :
benzazepines , Perbromination , Azepanone , Dieckmann condensation , azepine , Suzuki coupling , Azepinone
