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Synthesis 2011(5): 764-768
DOI: 10.1055/s-0030-1258422
DOI: 10.1055/s-0030-1258422
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of 2-Aminoindole-3-carboxylic Acid Derivatives by the Copper(I) Iodide Catalyzed Reaction of N-(2-Iodophenyl)formamides with Malononitrile or Cyanoacetates
Further Information
Received
9 November 2010
Publication Date:
03 February 2011 (online)
Publication History
Publication Date:
03 February 2011 (online)
Abstract
An efficient method for the synthesis of 2-aminoindole-3-carbonitriles and 2-aminoindole-3-carboxylates by the reaction of N-(2-iodophenyl)formamides with malononitrile and cyanoacetates, respectively, in the presence of a catalytic amount of copper(I) iodide using potassium carbonate as a base is reported.
Key words
2-aminoindole-3-carboxylates - 2-aminoindole-3-carbonitriles - N-(2-iodophenyl)formamides - copper(I) iodide - coupling
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1a
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3a A
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3b
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References
Before subjection to column chromatography on silica gel, the mixture must be filtered through a small pad of neutral alumina. Omission of this filtration procedure did not give 3a in a satisfactory purity. For details, see the experimental section.