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Molecules 2008, 13(1), 195-203; doi:10.3390/molecules13010195
Article

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

* ,  and
Chemistry Department, Faculty of Science, EL-Minia University, El-Minia 61519, A. R. Egypt
* Author to whom correspondence should be addressed.
Received: 30 November 2006 / Accepted: 25 February 2007 / Published: 30 January 2008
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Abstract

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.
Keywords: 6-Azido-5-formyl-2-pyridones; arylamines; Schiff bases; NMR spectroscopy. 6-Azido-5-formyl-2-pyridones; arylamines; Schiff bases; NMR spectroscopy.
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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Mekheimer, R.A.; Hameed, A.M.A.; Sadek, K.U. 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 2008, 13, 195-203.

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