First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines
Some novel Schiff bases have been prepared by reacting 6-azido-5-formyl-2-pyridone 1 with a series of aromatic amines 2a-f. 5-Arylaminomethylene-6-(E)-aryliminopyridones3a-e were obtained by reaction of 1 with 2a-e at room temperature,whereas with 2f, the 6-azido-5-naphthalen-2-yl-iminomethylpyridon...
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| Format: | Article |
| Language: | English |
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MDPI AG
2008-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/13/1/195/ |
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| author | Kamal U. Sadek Afaf M. Abdel Hameed Ramadan A. Mekheimer |
| author_facet | Kamal U. Sadek Afaf M. Abdel Hameed Ramadan A. Mekheimer |
| author_sort | Kamal U. Sadek |
| collection | DOAJ |
| description | Some novel Schiff bases have been prepared by reacting 6-azido-5-formyl-2-pyridone 1 with a series of aromatic amines 2a-f. 5-Arylaminomethylene-6-(E)-aryliminopyridones3a-e were obtained by reaction of 1 with 2a-e at room temperature,whereas with 2f, the 6-azido-5-naphthalen-2-yl-iminomethylpyridone derivative 4 wasformed. On the other hand, heating 1 with 2a-d at 140-150°C yielded two sets of isomericproducts, (E)-3a-d and (Z)-5a-d. Refluxing compounds (Z)-3a,c with hydroxyl-amine inmethanol gave the corresponding hydroxyliminopyridones 8a,c. Heating of (E)-3a-d withexcess POCl3 at reflux did not give the expected tricyclic compound 9, but rather theisomeric products (Z)-5a-d were obtained. The structures of all these products have beencharacterized using IR and 1H- and 13C-NMR spectroscopy. |
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| format | Article |
| id | doaj.art-3a05ba5b3dfc4c82a7bca1a19fcceda3 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-17T15:21:38Z |
| publishDate | 2008-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3a05ba5b3dfc4c82a7bca1a19fcceda32022-12-21T21:43:23ZengMDPI AGMolecules1420-30492008-01-0113119520310.3390/molecules13010195First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic AminesKamal U. SadekAfaf M. Abdel HameedRamadan A. MekheimerSome novel Schiff bases have been prepared by reacting 6-azido-5-formyl-2-pyridone 1 with a series of aromatic amines 2a-f. 5-Arylaminomethylene-6-(E)-aryliminopyridones3a-e were obtained by reaction of 1 with 2a-e at room temperature,whereas with 2f, the 6-azido-5-naphthalen-2-yl-iminomethylpyridone derivative 4 wasformed. On the other hand, heating 1 with 2a-d at 140-150°C yielded two sets of isomericproducts, (E)-3a-d and (Z)-5a-d. Refluxing compounds (Z)-3a,c with hydroxyl-amine inmethanol gave the corresponding hydroxyliminopyridones 8a,c. Heating of (E)-3a-d withexcess POCl3 at reflux did not give the expected tricyclic compound 9, but rather theisomeric products (Z)-5a-d were obtained. The structures of all these products have beencharacterized using IR and 1H- and 13C-NMR spectroscopy.http://www.mdpi.com/1420-3049/13/1/195/6-Azido-5-formyl-2-pyridonesarylaminesSchiff basesNMR spectroscopy. |
| spellingShingle | Kamal U. Sadek Afaf M. Abdel Hameed Ramadan A. Mekheimer First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines Molecules 6-Azido-5-formyl-2-pyridones arylamines Schiff bases NMR spectroscopy. |
| title | First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines |
| title_full | First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines |
| title_fullStr | First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines |
| title_full_unstemmed | First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines |
| title_short | First Synthesis and Isolation of the E- and Z-Isomers of Some New Schiff Bases. Reactions of 6-Azido-5-Formyl-2-Pyridone with Aromatic Amines |
| title_sort | first synthesis and isolation of the e and z isomers of some new schiff bases reactions of 6 azido 5 formyl 2 pyridone with aromatic amines |
| topic | 6-Azido-5-formyl-2-pyridones arylamines Schiff bases NMR spectroscopy. |
| url | http://www.mdpi.com/1420-3049/13/1/195/ |
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