Collect. Czech. Chem. Commun. 1990, 55, 2715-2721

Studies in Vilsmeier-Haack reaction. Application to quinoxalinones

Ibrahim M. A. Awad and Khairy M. Hassan

Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt


The 3-methyl group in quinoxalinones I and II has been found to undergo diformylation by Vilsmeier reagent to give the corresponding aminoacrolein derivatives (III, IV). Condensation and/or interaction of III or IV with some secondary heterocyclic amines and/or with hydrazine, phenylhydrazine and hydroxylamine affords the related 3-methyl-N-(1H)-2-quinoxalinone and 1,3-dimethyl-2-quinoxalinone derivatives (VII-XVIII), some with pronounced fluorescence activities. All synthesized compounds have been screened in vitro for their antimicrobial activities against Gram-positive and Gram-negative bacteria. The structures of these compounds were confirmed by elemental analysis, IR and 1H NMR spectroscopy.