Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N'-arylureas
Ring expansion and ring opening of 3-halooxindoles with N-alkoxycarbonyl-O-tosylhydroxylamines for divergent access to 4-aminoquinolin-2-ones and N-Cbz-N'-arylureas
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DOI：
10.1039/d0qo01335h
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发表时间：
2021-02-21
影响因子：
5.4
通讯作者：
You，Yong
中科院分区：
文献类型：
--
作者：
Yuan，Wei-Cheng;Zuo，Jian;You，Yong
开发了一种用于 3-卤代吲哚扩环和开环的不同方法。在温和的碱介导条件下，3-卤代吲哚原位生成吲哚酮，然后与 N-烷氧基羰基-O-甲苯磺酰羟胺顺利反应，通过扩环和开环途径分别以良好至优异的产率生成 4-氨基喹啉-2-酮和 N-Cbz-N'-芳基脲。该方案的特点是底物容易获得、反应条件友好、官能团耐受性广、操作程序简单。
A divergent method for ring expansion and ring opening of 3-halooxindoles has been developed. Under mild base-mediated conditions, 3-halooxindoles generate indolones in situ, which then react smoothly with N-alkoxycarbonyl-O-tosylhydroxylamines to give 4-aminoquinolin-2-ones and N-Cbz-N′-arylureas in good to excellent yields via ring expansion and opening pathways, respectively. This protocol is characterized by easy availability of substrates, user-friendly reaction conditions, broad functional group tolerance, and a simple operation procedure.