Synthesis and Chemistry of 3-Amino- and 3-Hydrazocarbonylquinoxalinone Derivatives

Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt
Manuscript received 4 June 1993, accepted 18 August 1993

3-Ethoxycarbonyl-2(1H)-quinoxalinone (1) reacts with nucleophiles, namely, dimethylamine, diethylamine, o- phenylenediamine and/or p-phenylenediamine to produce the corresponding 3-N-substituted-aminocarbonyl-2(1H)-quinoxalinones (3-6). Treatment of 1 with hydrazine hydrate produces the 2(1H)-quinoxalinone-3-carbohydrazide (2) with acylating reagents, namely, acetic anhydride, acetic acid or acetyl chloride/pyridine, phenylisothiocyanate, p-toluene-sulphonyl chloride and/or diethylmalonate to produce the corresponding 3-β-N-substituted-hydrazocar-boxyl-2(1H)-quinoxalines (7-10, 12). Condensation of 2 with benzaldehyde, p-anisaldehyde, p-N-dimethylaminobenzaldehyde andlor p-nitrobenzaldehyde gives the corresponding 3-arylidenehydrazocarbonyl-2(1H)-quinoxalinones (Ha-d). Treatment of 2 with acetylacetone gives 3-(3,5-dimethylpyrazol-1-yl-carbonyl)-2(1H)-quinoxaline (13). Diazodisation of 2 produces 2(1H)-quinoxalinone-3-carboazide (14) which when treated with absolute ethanol and/or t-butanol produces the corresponding 3-alkoxycarbonylaminoquinoxalinones (15,16) and the both cyclise on treatment with hydrazine hydrate into triazinoquinoxaline (17).