SYNTHESIS AND CHEMISTRY OF 3-AMINOQUINOXALINONE AND 3-HYDRAZOCARBONYLQUINOXALINONE DERIVATIVES

3-Ethoxycarbonyl-2(1H)-quinoxalinone (1) reacts with nucleophiles, nam ely, dimethylamine, diethylamine, o-phenylenediamine and/or p-phenylen ediamine to produce the corresponding 3-N-substituted-aminocarbonyl-2( 1H)-quinoxalinones (3-6), Treatment of 1 with hydrazine hydrate produc es the 2(1H)-quinoxalinone-3-carbohydrazide (2) with acylating reagent s, namely, acetic anhydride, acetic acid or acetyl chloride/pyridine, phenylisothiocyanate, p-toluene-sulphonyl chloride and/or diethylmalon ate to produce the corresponding a-N-substituted-hydrazocarboxyl-2(1H) -quinoxalines (7-10, 12). Condensation of 2 with benzaldehyde, p-anisa ldehyde, p-N-dimethylaminobenzaldehyde and/or p-nitrobenzaldehyde give s the corresponding 3-arylidenehydrazocarbonyl-2(1H)-quinoxalinones (1 1a-d). Treatment of 2 with acetylacetone gives 5-dimethylpyrazol-1-yl- carbonyl)-2(1H)-quinoxaline (13). Diazodisation of 2 produces 2(1H)-qu inoxalinone-3-carboazide (14) which when treated with absolute ethanol and/or t-butanol produces the corresponding 3-alkoxycarbonylaminoquin oxalinones (15, 16) and the both cyclise on treatment with hydrazine h ydrate into triazinoquinoxaline (17).