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

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The first example of silver-promoted [3+4] cycloaddition of α-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… Click to show full abstract

The first example of silver-promoted [3+4] cycloaddition of α-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.

Keywords: dearomative cycloaddition; cycloaddition anthranils; silver promoted; promoted dearomative; access; cycloaddition

Journal Title: Chemical communications
Year Published: 2022

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