Concise Synthesis of Furo[2,3-b]indolines via [3,3]-Sigmatropic Rearrangement of N-Alkenyloxyindoles
Concise Synthesis of Furo[2,3-b]indolines via [3,3]-Sigmatropic Rearrangement of N-Alkenyloxyindoles
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DOI：
10.1055/s-0040-1707250
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发表时间：
2020-08-27
期刊：
影响因子：
2
通讯作者：
Anderson, Laura L.
中科院分区：
文献类型：
--
作者：
Shevlin, Michael;Strotman, Neil A.;Anderson, Laura L.
利用N-烯氧基吲哚中间体的反应活性，发展了一条合成呋喃并[2，3-B]吲哚啉的新路线。这些化合物自发地进行[3，3]-σ转移重排，然后环化形成半缩醛作为单一的非对映异构体。锡促进的N-羟基吲哚形成，然后与活化的炔进行共轭加成，提供了简单和模块化的方法来获得各种各样的N-烯氧基吲哚及其相应的呋喃并[2，3-B]吲哚啉。微型高通量实验，以方便调查的范围和宽容的这种转变和相关研究的亲核芳香取代和重排的N-羟基吲哚与卤代芳烃也进行了评估。
A concise new synthetic route to furo[2,3-b]indolines has been developed by taking advantage of the reactivity of N-alkenyloxyindole intermediates. These compounds spontaneously undergo [3,3]-sigmatropic rearrangement followed by cyclization to form hemiaminals as single diastereomers. Tin-promoted N-hydroxyindole formation followed by conjugate addition to activated alkynes provides simple and modular access to a diverse array of N-alkenyloxyindoles and their corresponding furo[2,3-b]indolines. Microscale high-throughput experimentation was used to facilitate investigation of the scope and tolerance of this transformation and related studies on the nucleophilic aromatic substitution and rearrangement of N-hydroxyindoles with halogenated arenes have also been evaluated.