biostudies-literatureUnknown12(10)Bai GThe 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.ACS medicinal chemistry letters1585-1588https://www.ebi.ac.uk/biostudies/studies/S-EPMC8521649biostudies-literatureIntramolecular Ring-Opening Decomposition of Aryl Azetidines.PMC8521649O'Connell TNBrodney MAOgilvie KYan JLi CSalomon-Ferrer RLaChapelle EAPhilippe LMcAllister LACzabaniuk LCShapiro MJButler CRGilbert AMBai GUccello DPBrown MFStarr JTWithka JMfalseIntramolecular Ring-Opening Decomposition of Aryl Azetidines.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.2021-01-01T00:00:00Z2021 Oct2025-04-04T21:42:06.666Z2025-04-04T21:42:06.666ZS-EPMC85216493467604010.1021/acsmedchemlett.1c00402