Concise Synthesis of Furo[2,3-b]indolines via [3,3]-Sigmatropic Rearrangement of N-Alkenyloxyindoles

被引:5
|
作者
Shevlin, Michael [1 ,2 ]
Strotman, Neil A. [1 ]
Anderson, Laura L. [2 ]
机构
[1] Merck & Co Inc, Dept Proc Res & Dev, 126 E Lincoln Ave, Rahway, NJ 07065 USA
[2] Univ Illinois, Dept Chem, 845 W Taylor St, Chicago, IL 60607 USA
基金
美国国家科学基金会;
关键词
N-hydroxyindole; 3,3]-sigmatropic rearrangement; heterocycle; hemiaminal; high-throughput experimentation; HIGH-THROUGHPUT EXPERIMENTATION; DRUG DISCOVERY; CHEMISTRY; ARYLHYDROXYLAMINES; PHYSOSTIGMINE; HETEROCYCLES; ARYLATION; METHYL;
D O I
10.1055/s-0040-1707250
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:197 / 201
页数:5
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