Synthesis of Azepinones

A new Rh(III)-catalyzed intermolecular annulation of Af-methoxybenzamides with a, -unsaturated aldehydes or ketones to afford azepinones 118 was reported by Glorias eta/. (Eq. (5.109)) [56a]. The reaction involves a tandem C-H activation, cyclization, and condensation sequence. The substrates with other A/-substituents, such as H, phenyl, and OPiv, did not afford the corresponding products. Vinylcarbenoids were also used as the three-carbon component in the Rh(III)-catalyzed C-H activation and [4-1-3] cycloaddition with benzamides to access azepinones (Eq. (5.110)) [56b]. 

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New results on phenyl azides include the optimization and up-scaling of the synthesis of azepinones by azide photorearrrangement and water addition to the didehydroazepine intermediate. This has been done in a... 

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