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

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
PDF Full-text Download PDF Full-Text [91 KB, uploaded 1 October 2008 09:18 CEST]
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.

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

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.

AMA Style

Mekheimer RA, Hameed AMA, Sadek KU. 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(1):195-203.

Chicago/Turabian Style

Mekheimer, Ramadan A.; Hameed, Afaf M.A.; Sadek, Kamal U. 2008. "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 13, no. 1: 195-203.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert