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Synthesis 1999; 1999(1): 46-48
DOI: 10.1055/s-1999-3669
short paper
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Synthesis of Cyanopyrroles

Lingjiang Cheng* , David A. Lightner
  • *Department of Chemistry, University of Nevada, Reno, Nevada 89557, USA; Fax 7 02-7 84-68 04
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Publication Date:
31 December 1999 (online)

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Regioselective synthesis of α-cyanopyrroles (vs. α-alkoxycarbonylpyrroles) using oximinocyanoacetate esters in a Knorr-type reductive condensation with β-diketones can be directed by the presence of water. Thus, methyl oximinocyanoacetate was reacted with pentane-2,4-dione in hot acetic acid in the presence of zinc dust to give exclusively 3,5-dimethylpyrrole-2-carbonitrile when the acetic acid was wet; whereas, in glacial acetic acid only methyl 3,5-dimethylpyrrole-2-carboxylate was isolated (∼40% yield).

α-cyanopyrroles - oximinocyanoacetate - Knorr-type reaction