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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
1 Applied Science Department, College of Technological Studies, Public Authority for Applied Education and Training, P. O. Box 42325 Safat, 70654, Kuwait 2 Chemistry Department, Kuwait University, P.O. Box 5969 Safat, 13060, Kuwait
* Author to whom correspondence should be addressed.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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