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)-aryl-iminopyridones 3a-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 was formed. On the other hand, heating 1 with 2a-d at 140-150 degrees C yielded two sets of isomeric products, (E)-3a-d and (Z)-5a-d. Refluxing compounds (Z)-3a,c with hydroxyl-amine in methanol gave the corresponding hydroxyliminopyridones 8a,c. Heating of (E)-3a-d with excess POCl3 at reflux did not give the expected tricyclic compound 9, but rather the isomeric products (Z)-5a-d were obtained. The structures of all these products have been characterized using IR and 1H- and 13C-NMR spectroscopy.
Mekheimer
Ramadan A
RA
Chemistry Department, Faculty of Science, EL-Minia University, El-Minia 61519, A. R. Egypt. rmekh@yahoo.com
Abdel Hameed
Afaf M
AM
Sadek
Kamal U
KU
D000588:Amines / Q000737:chemistry*; D007536:Isomerism; D011728:Pyridones / Q000138:chemical synthesis / Q000737:chemistry*; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification
C526934:6-azido-5-formyl-2-pyridone; D000588:Amines; D011728:Pyridones; D012545:Schiff Bases