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

Ramadan A. Mekheimer¹  Afaf M. Abdel Hameed² 

[1] Chemistry Department, Faculty of Science, EL-Minia University, El-Minia 61519, A. R. Egypt; E-mail

关键词: 6-Azido-5-formyl-2-pyridones;    6-Azido-5-formyl-2-pyridones;    arylamines;    Schiff bases;    NMR spectroscopy;   

DOI  :  10.3390/molecules13010195

来源: mdpi

【 摘 要 】

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°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.

【 授权许可】

Unknown   
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