1341858-38-5Relevant articles and documents
Unusual Skeletal Reorganization of Oxetanes for the Synthesis of 1,2-Dihydroquinolines
Guo, Wengang,Huang, Hai,Qian, Chenxiao,Sun, Jianwei,Wang, Guannan
, p. 11245 - 11249 (2020)
Skeletal reorganization is a type of fascinating transformations owing to their intriguing mechanisms and utility in complex molecule synthesis. However, only a limited amount of examples are known for most functional groups. Herein, we describe such an unusual process of oxetanes. In the presence of In(OTf)3 as catalyst, oxetane-tethered anilines reacted unexpectedly to form 1,2-dihydroquinolines. This process not only provides expedient access to dihydroquinolines, but also represents a new reaction of oxetane. Mechanistically, it is believed that the reaction proceeds through initial nitrogen attack rather than arene attack followed by a series of bond cleavage and formation events. Control experiments provided important insights into the mechanism.
