Mekheimer Ramadan A, Abdel Hameed Afaf M, Sadek Kamal U
Chemistry Department, Faculty of Science, EL-Minia University, El-Minia 61519, A. R. Egypt.
Molecules. 2008 Jan 30;13(1):195-203. doi: 10.3390/molecules13010195.
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.
通过使6-叠氮基-5-甲酰基-2-吡啶酮1与一系列芳香胺2a - f反应，制备了一些新型席夫碱。在室温下，1与2a - e反应得到5-芳氨基亚甲基-6-(E)-芳基亚氨基吡啶酮3a - e，而与2f反应则形成6-叠氮基-5-萘-2-基亚氨基甲基吡啶酮衍生物4。另一方面，在140 - 150℃下将1与2a - d加热得到两组异构体产物，(E)-3a - d和(Z)-5a - d。在甲醇中，将(Z)-3a,c与羟胺回流得到相应的羟基亚氨基吡啶酮8a,c。将(E)-3a - d与过量的POCl3在回流条件下加热，并未得到预期的三环化合物9，而是得到了异构体产物(Z)-5a - d。所有这些产物的结构均通过红外光谱、1H - NMR和13C - NMR光谱进行了表征。
