Cesium Carbonate Mediated Cyclization of Oxotryptamines with Allenoates: An Approach to Spiro[azepane-4,3′-indol]-2′(1′H)-ones

A new method was developed for the synthesis of spiro[azepane-4,3'-indol]-2'(1'H)-ones in yields of up to 96% with a broad substrate scope by using oxotryptamines as dual-nucleophilic reagents to react with allenoates in the presence of cesium carbonate under mild conditions. In accord with previous works and a deprotonation-tracing experiment, a plausible reaction mechanism is proposed.

Automated summary

A new method has been developed for the synthesis of spiro[azepane-4,3'-indol]-2'(1'H)-ones with yields of up to 96%, using oxotryptamines as dual-nucleophilic reagents to react with allenoates in the presence of cesium carbonate under mild conditions. A plausible reaction mechanism is proposed based on previous works and a deprotonation-tracing experiment.