37896-13-2Relevant academic research and scientific papers
Oxidative Desymmetrization of Isoindolines Realized by tert -Butyl Nitrite (TBN) Initiated Radical sp 3C-H Activation Relay (CHAR)
Sun, Zheng,Shao, Yu,Zhang, Shuwei,Zhang, Yuxian,Yuan, Yu,Jia, Xiaodong
, p. 1663 - 1671 (2021/02/01)
An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp 3C-H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N -alkyl iso-indolines can be well tolerated. The mechanistic study shows that the C-H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.
Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome
Jha, Amitabh,Chou, Ting-Yi,ALJaroudi, Zainab,Ellis, Bobby D.,Cameron, T. Stanley
supporting information, p. 848 - 857 (2014/05/06)
The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.
