Synthesis of Substituted Indole from 2-Aminobenzaldehyde through [1,2]-Aryl Shift

被引：52

作者：

Levesque, Patrick ^{[1
]}

Fournier, Pierre-Andre ^{[1
]}

机构：

[1] Merck Frosst Ctr Therapeut Res, Kukland, PQ H9H 3L1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 20期

关键词：

ALKALOIDS; ACCESS; DEBENZYLATION; CONSTRUCTION; INSERTION; BOND;

D O I：

10.1021/jo1016713

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild, efficient and simple method for the synthesis of 3-ethoxycarbonylindoles had been developed. Addition of ethyl diazoacetate (EDA) to 2-aminobenadehydes cleanly affords the indole core. As opposed to other common approaches for the synthesis of indole, this method displays both excellent functional group tolerance and perfect regiochemical control. This allowed the synthesis of a variety of useful indole building blocks from 2-aminobenzaldehydes derived from readily available anthranilie acids.

引用

页码：7033 / 7036

页数：4

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