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Synthesis 2008(15): 2462-2466  
DOI: 10.1055/s-2008-1067159
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 4-Hydroxy-1H-pyrrole-2,3-dicarboxylic Acid Derivatives: Unusual Coupling of Acetylenic Esters and α-Amino Acids in the Presence of Cyclohexyl Isocyanide or N,N′-Dicyclohexylcarbodiimide

Abdolali Alizadeh*, Reza Hosseinpour, Sadegh Rostamnia
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran 18716, Iran
Fax: +98(21)88006544; e-Mail: aalizadeh@modares.ac.ir;
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Publication History

Received 3 April 2008
Publication Date:
08 July 2008 (online)

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Abstract

A facile and direct synthetic entry to 4-hydroxy-1H-pyrrole-2,3-dicarboxylic acid derivatives is reported. It is based on the unusual ring annulation of acetylenic esters and α-amino acids with isocyanide or carbodiimide under neutral conditions in a one-step procedure.

Key words

pyrroles - α-amino acids - alkynes - isocyanides - N,N′-dicyclohexylcarbodiimide

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