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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

Author(s): Ramadan A. Mekheimer | Afaf M. Abdel Hameed | Kamal U. Sadek

Journal: Molecules
ISSN 1420-3049

Volume: 13;
Issue: 1;
Start page: 195;
Date: 2008;
Original page

Keywords: 6-Azido-5-formyl-2-pyridones | arylamines | Schiff bases | NMR spectroscopy.

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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