Metal-free and regiospecific synthesis of 3-arylindoles
Metal-free and regiospecific synthesis of 3-arylindoles
复制标题
3-芳基吲哚的无金属和区域特异性合成
DOI：
10.1039/d0ob00317d
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发表时间：
2020
影响因子：
3.2
通讯作者：
Xu Jiaxi
中科院分区：
文献类型：
--
作者：
Xu Chuangchuang;Xie Wenlai;Xu Jiaxi
以3-芳基环氧乙烷-2-腈和芳基肼盐酸盐为原料，发展了一种简便、无金属、有机酸碱促进的合成3-芳基吲哚的方法。在该反应中，有机酸催化芳环氧乙烷腈和芳肼盐酸盐的串联亲核开环反应和Fischer吲哚化。有机碱三乙胺在Fischer吲哚合成的最后消除步骤中起着至关重要的作用，区域特异性地提供3-芳基吲哚。该反应具有微波加速、非金属参与、反应时间短、有机酸碱共催化、底物范围广等优点。
A convenient, metal-free, and organic acid–base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid–base co-catalysis, and broad substrate scope.