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

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 chlo...

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Autores principales: Alnajjar, Abdul-aziz, Abdelkhalik, Mervat Mohammed, Al-Enezi, Amal, Elnagdi, Mohamed Hilmy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2008
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254057/
https://www.ncbi.nlm.nih.gov/pubmed/19127238
http://dx.doi.org/10.3390/molecules14010068
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author Alnajjar, Abdul-aziz
Abdelkhalik, Mervat Mohammed
Al-Enezi, Amal
Elnagdi, Mohamed Hilmy
author_facet Alnajjar, Abdul-aziz
Abdelkhalik, Mervat Mohammed
Al-Enezi, Amal
Elnagdi, Mohamed Hilmy
author_sort Alnajjar, Abdul-aziz
collection PubMed
description 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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spelling pubmed-62540572018-11-30 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 Alnajjar, Abdul-aziz Abdelkhalik, Mervat Mohammed Al-Enezi, Amal Elnagdi, Mohamed Hilmy Molecules Article 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. Molecular Diversity Preservation International 2008-12-29 /pmc/articles/PMC6254057/ /pubmed/19127238 http://dx.doi.org/10.3390/molecules14010068 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Alnajjar, Abdul-aziz
Abdelkhalik, Mervat Mohammed
Al-Enezi, Amal
Elnagdi, Mohamed Hilmy
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254057/
https://www.ncbi.nlm.nih.gov/pubmed/19127238
http://dx.doi.org/10.3390/molecules14010068
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