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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; in revised form: 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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MDPI and ACS Style

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.

AMA Style

Alnajjar A-A, Abdelkhalik MM, Al-Enezi A, Elnagdi MH. 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(1):68-77.

Chicago/Turabian Style

Alnajjar, Abdul-Aziz; Abdelkhalik, Mervat Mohammed; Al-Enezi, Amal; Elnagdi, Mohamed Hilmy. 2009. "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 14, no. 1: 68-77.



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