1303507-91-6Relevant articles and documents
The synthesis of multi-substituted pyrrolidinones: Via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes
Zhang, Yixin,Ma, Haojie,Liu, Xingxing,Cui, Xinfeng,Wang, Shaohua,Zhan, Zhenzhen,Pu, Jinghong,Huang, Guosheng
supporting information, p. 4439 - 4442 (2018/06/29)
A novel [3 + 2] cycloaddition reaction of azaoxyallyl cations and aromatic ethylenes has been developed to afford multi-substituted pyrrolidinones in moderate to good yields. This method not only further expands the synthetic utility of α-halo hydroxamate
Dearomative Indole (3 + 2) Reactions with Azaoxyallyl Cations - New Method for the Synthesis of Pyrroloindolines
DiPoto, Maria C.,Hughes, Russell P.,Wu, Jimmy
supporting information, p. 14861 - 14864 (2015/12/08)
Herein, we report the first examples of the synthesis of pyrroloindolines by means of (3 + 2) dearomative annulation reactions between 3-substituted indoles and highly reactive azaoxyallyl cations. Computational studies using density functional theory (DFT) (B3LYP-D3/6-311G++) support a stepwise reaction pathway in which initial C-C bond formation takes place at C3 of indole, followed by ring closure to give the observed products. Insights gleaned from these calculations indicate that the solvent, either TFE or HFIP, can stabilize the transition state through H-bonding interactions with oxygen of the azaoxyallyl cation and other relevant intermediates, thereby increasing the rates of these reactions.
