Reactions of azepinones with electrophiles

Azepinones are available via a one-pot cycloaddition-ring expansion reaction sequence in good yield. The reactions of azepinones with alkyl halides and epoxides were studied. We report herein protocols for the alkylation of azepinones at nitrogen with alkyl halides and epoxides and the isomerizations that occur in the presence of a base. We also report an unexpected ring contraction under oxidative conditions.