Synthesis and transformations of ethyl 3-(Benzoylamino)-1H-indole-2-carboxylates

被引：11

作者：

Cucek, Karmen ^{[1
]}

Vercek, Bojan ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

来源：

SYNTHESIS-STUTTGART | 2008年 / 11期

关键词：

hydrazones; indoles; cyclization; Fischer indole synthesis; rearrangement;

D O I：

10.1055/s-2008-1067025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of ethyl 3-(benzoylamino)-1H-indole-2-carboxylates were prepared by heating ethyl 2-(benzoylamino)-3-(phenylhydrazono)propanoates with polyphosphoric acid. The reaction of ethyl 3-(benzoylamino)-5-chloro-1H-indole-2-carboxylate with hydrazine hydrate resulted in the formation of the debenzoylated hydrazide. Hydrolysis of the same ester with aqueous sodium hydroxide afforded 3-(benzoylamino)-5-chloro-1H-indole-2-carboxylic acid, which on heating underwent a decarboxylation reaction to give N-(5-chloro-1H-indol-3-yl)benzainide.

引用

页码：1741 / 1746

页数：6

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