伊萨丁
亚胺
原位
环加成
化学
甲亚胺叶立德
组合化学
有机化学
催化作用
1,3-偶极环加成
作者
Lei Zhang,Ying Liu,Yongzhu Zhou
标识
DOI:10.1002/slct.202104059
摘要
Abstract The cycloaddition reactions between isatin azomethine imine and in situ generated azaoxyallyl cation were explored by density functional theory calculations to elucidate the competition among different pathways. The [3+2] cycloaddition between azaoxyallyl cation and carbonyl group could proceed via either the N‐alkylated pathway or O‐alkylated pathway, which finally afforded the 4‐oxazolidinone or imidate skeleton, respectively. The exclusive formation of the 4‐oxazolidinone product should result from the higher stability and feasible conversion. The possibly competing [3+3] reaction between azaoxyallyl cation and azomethine imine was predicted to be less favorable kinetically than the [3+2] one. Lastly, charge and orbital analyses were performed on isatin azomethine imine to explain the observed reactivities.
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