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Synthesis 2008(11): 1741-1746  
DOI: 10.1055/s-2008-1067025
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Transformations of Ethyl 3-(Benzoylamino)-1H-indole-2-carboxylates

Karmen Čuček, Bojan Verček*
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Akerčeva 5, 1000 Ljubljana, Slovenia
Fax: +386(1)2419220; e-Mail: bojan.vercek@fkkt.uni-lj.si;
Further Information

Publication History

Received 29 January 2008
Publication Date:
16 April 2008 (online)

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Abstract

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)benzamide.

Key words

hydrazones - indoles - cyclization - Fischer indole synthesis - rearrangement

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