Intramolecular Ring-Opening Decomposition of Aryl Azetidines.
Guoyun BaiThomas N O'ConnellMichael A BrodneyChristopher R ButterLara C CzabaniukAdam M GilbertErik A LaChapelleChao LiLaura A McAllisterKevin OgilvieLaurence PhilippeRomelia Salomon-FerrerMichael J ShapiroJeremy T StarrDaniel P UccelloJane M WithkaJiangli YanMatthew F BrownPublished in: ACS medicinal chemistry letters (2021)
The ring strain present in azetidines can lead to undesired stability issues. Herein, we described a series of N-substituted azetidines which undergo an acid-mediated intramolecular ring-opening decomposition via nucleophilic attack of a pendant amide group. Studies were conducted to understand the decomposition mechanism enabling the design of stable analogues.