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Molecules 2009, 14(1), 68-77; doi:10.3390/molecules14010068
Article

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

1, 1,* , 1 and 2
Received: 16 November 2008 / Revised: 15 December 2008 / Accepted: 17 December 2008 / Published: 29 December 2008
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Abstract

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.
Keywords: Enaminones; 2-Cyano-5-(dimethylamino)-5-arylpenta-2; 4-dienamide; DEPT; Experiments; X-ray crystal structure Enaminones; 2-Cyano-5-(dimethylamino)-5-arylpenta-2; 4-dienamide; DEPT; Experiments; X-ray crystal structure
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Alnajjar, A.-A.; Abdelkhalik, M.M.; Al-Enezi, A.; Elnagdi, M.H. 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. Molecules 2009, 14, 68-77.

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