Zheng Fuqiang, Zhou Jianhui, Fang Feifei, Li Jiyuan, Wang Jing, Zheng Miao, Liu Hong, Xu Yungen, Zhou Yu
Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China.
Org Lett. 2022 Aug 12;24(31):5688-5692. doi: 10.1021/acs.orglett.2c02070. Epub 2022 Aug 3.
A Rh(III)-catalyzed C-H activation of α-keto oximes and a cyclization cascade with diazo compounds were developed to construct the highly fused indano[1,2-]azirine frameworks in good yields with a broad range of substrates under mild reaction conditions. More intriguingly, a [4+1+1] sequential annulation cascade is demonstrated for the first time in this reaction and opened a new reaction mode for α-keto oximes. These fused indano[1,2-]azirine derivatives could also be further transformed into intriguing privileged drug scaffolds.
开发了一种铑（III）催化的α-酮肟的C-H活化反应以及与重氮化合物的环化串联反应，可在温和的反应条件下，以良好的产率、适用于多种底物构建高度稠合的茚并[1,2 -]氮丙啶骨架。更有趣的是，该反应首次展示了[4+1+1]顺序环化串联反应，并为α-酮肟开辟了一种新的反应模式。这些稠合的茚并[1,2 -]氮丙啶衍生物还可进一步转化为引人关注的优势药物骨架。
