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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2008-12-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/14/1/68/ |
| _version_ | 1831833860261806080 |
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| author | Mohamed Hilmy Elnagdi Amal Al-Enezi Mervat Mohammed Abdelkhalik Abdul-Aziz Alnajjar |
| author_facet | Mohamed Hilmy Elnagdi Amal Al-Enezi Mervat Mohammed Abdelkhalik Abdul-Aziz Alnajjar |
| author_sort | Mohamed Hilmy Elnagdi |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-23T04:02:36Z |
| format | Article |
| id | doaj.art-dcdad2727be740a6a2bc55e9e827fae6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T04:02:36Z |
| publishDate | 2008-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-dcdad2727be740a6a2bc55e9e827fae62022-12-21T18:00:43ZengMDPI AGMolecules1420-30492008-12-01141687710.3390/molecules14010068Enaminones 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 AcidsMohamed Hilmy ElnagdiAmal Al-EneziMervat Mohammed AbdelkhalikAbdul-Aziz AlnajjarThe 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.http://www.mdpi.com/1420-3049/14/1/68/Enaminones2-Cyano-5-(dimethylamino)-5-arylpenta-24-dienamideDEPTExperimentsX-ray crystal structure |
| spellingShingle | Mohamed Hilmy Elnagdi Amal Al-Enezi Mervat Mohammed Abdelkhalik Abdul-Aziz Alnajjar 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 Enaminones 2-Cyano-5-(dimethylamino)-5-arylpenta-2 4-dienamide DEPT Experiments X-ray crystal structure |
| 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 | Enaminones 2-Cyano-5-(dimethylamino)-5-arylpenta-2 4-dienamide DEPT Experiments X-ray crystal structure |
| url | http://www.mdpi.com/1420-3049/14/1/68/ |
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