Intramolecular Ynamide-Benzyne (3+2) Cycloadditions

被引：9
|
作者：
Tawatari, Tsukasa [1 ]
Kato, Ritsuki [1 ]
Kudo, Riku [1 ]
Takasu, Kiyosei [1 ]
Takikawa, Hiroshi [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 19期
基金：
日本学术振兴会;
关键词：
Benzyne; Cycloaddition; Heterocycles; Ylides; Ynamides; 1,3-DIPOLAR CYCLOADDITION; NUCLEOPHILIC-SUBSTITUTION; SELECTIVE SYNTHESIS; NITRILE OXIDES; N-ARYLINDOLES; ARYNES; EFFICIENT; NITROGEN; BENZOTRIAZOLES; 1H-INDAZOLES;
D O I：
10.1002/anie.202300907
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report herein intramolecular (3+2) cycloaddition reactions between ynamides as three-atom components and benzyne. In these intramolecular reactions, the two-bond formation is realized by exploiting benzyne precursors that contain a chlorosilyl group as a linking functionality. This method thus highlights the ambivalent character of the intermediate indolium ylide, which exhibits both nucleophilic and electrophilic properties at its C2 atom.
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页数：6
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