Silver-promoted dearomative [3+4] cycloaddition of anthranils with α-isocyanoacetates: access to benzodiazepines

The first example of silver-promoted [3+4] cycloaddition of alpha-isocyanoacetates with anthranils as aromatic Michael accepters, offering access to benzo[d][1,3]diazepinones, has been developed. Mechanistic studies revealed that an oxygen migration rearrangement process was involved in this dearomative cycloaddition reaction. Additionally, benzo[d][1,3]diazepinones were obtained efficiently as well under catalytic conditions. Broad functional groups were well tolerated under mild reaction conditions.

Automated summary

In this study, a silver-promoted [3+4] cycloaddition reaction between alpha-isocyanoacetates and anthranils was developed, leading to the synthesis of benzo[d][1,3]diazepinones. Mechanistic studies revealed an oxygen migration rearrangement process involved in this dearomative cycloaddition reaction. Additionally, catalytic conditions efficiently yielded benzo[d][1,3]diazepinones, while tolerating a wide range of functional groups under mild reaction conditions.