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.docVIP

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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.doc

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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

Molecules 2009, 14, 68-77; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules 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 Abdul-aziz Alnajjar 1, Mervat Mohammed Abdelkhalik 1,*, Amal Al-Enezi 1 and Mohamed Hilmy Elnagdi 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; E-mail: mervatak@. Received: 16 November 2008; in revised form: 15 December 2008 / Accepted: 17 December 2008 / Published: 29 December 2008 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. Introduction Enaminones are polydentate reagents that have been utilized extensively in this decade as building blocks in organic synthesis [1-6]. In previous work at our laboratories, we reported several efficient routes to polyfunctionally substituted heterocycles utilizing enaminones as starting materials [7-11]. We have also reported that the reaction of 1a with malononitrile in ethanolic sodium ethoxide afforded Molecules 2009, 14 69 2a in good yield [12], while reac