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Enaminones As Building Blocks In Heterocyclic Syntheses: Reinvestigating The Product Structures Of Enaminones With Malononitrile. A Novel Route To 6-Substituted-3-Oxo-2,3-Dihydropyridazine-4-Carboxylic Acids

A. Al-Najjar, M. Abdelkhalik, Amal Al-Enezi, M. H. Elnagdi
Published 2008 · Chemistry, Medicine

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The reported structures of reaction products of enaminones with malononitrile in ethanolic piperidine are revised. A novel route to 2,3-dihydropyridazine-4-carboxylic acids 4a-c via reactions of 2-cyano-5-(dimethylamino)-5-arylpenta-2,4-dienamides 8a-c with nitrous acid or with benzenediazonium chloride is reported. Compounds 8a-c are converted to 1,2-dihydropyridine-3-carboxylic acid and 1,2-dihydropyridine-3-carbonitrile derivatives upon reflux in EtOH/ HCl and in AcOH.
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