The catalyst‐controlled diversity‐oriented synthesis of spirohydroquinoline‐indandiones and 3‐methylenehydroquinoline‐indandiones from ortho‐sulfonamidophenyl‐substituted para‐quinone methides and allylidene‐indandiones is reported. The strategies utilized an organobase such as DMAP or TMG to control the reaction pathway chemoselectively, furnishing the corresponding products in 40–99% yields with excellent diastereoselectivities. The mechanistic studies revealed that spirohydroquinoline‐indandione was the kinetic product to afford 3‐methylenehydroquinoline‐indandione in the presence of TMG, which probably involved an unusual base‐initiated 1,3‐nitrogen rearrangement process.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.