Department of Chemistry , University of Minnesota , 207 Pleasant Street SE , Minneapolis , Minnesota 55455 , United States.
Org Lett. 2018 Dec 21;20(24):8082-8085. doi: 10.1021/acs.orglett.8b03439. Epub 2018 Dec 11.
Reactions of thermally generated benzynes with diaziridines are reported. These trapping reactions follow the same pathway as reported earlier by Heine and co-workers with electron-deficient alkynes. The resulting N-arylhydrazones were obtained efficiently in a single step. The preference for the mode of addition of the nucleophilic diaziridine nitrogen atom to the more electrophilic benzyne carbon was consistent with what is predicted on the basis of distortion analysis. The feasibility of converting the hydrazone into a Fisher-indole adduct was demonstrated.
本文报道了偕二氮丙环与热生成的苯炔之间的反应。这些捕获反应遵循与海因及其同事之前报道的缺电子炔烃相同的途径。所得的 N-芳基腙可以在一步中有效地得到。亲核的偕二氮丙环氮原子加成到更富电子的苯炔碳上的方式的偏好与基于扭曲分析预测的结果一致。还证明了将腙转化为 Fisher-吲哚加合物的可行性。
