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Synthesis 1999; 1999(1): 46-48
DOI: 10.1055/s-1999-3669
DOI: 10.1055/s-1999-3669
short paper
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Synthesis of Cyanopyrroles
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Publikationsverlauf
Publikationsdatum:
31. Dezember 1999 (online)
![](https://www.thieme-connect.de/media/synthesis/199901/lookinside/thumbnails/10.1055-s-1999-3669-1.jpg)
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