Ethoxycarbonylmethylation of 3- [1-penylhydrazono-L-threo-2,3,4-trihydroxybutyl] -1H-quinoxalin-2-one

ABSTRACT

Reaction of 3-[1-phenylhydrazono-L-threo-2, 3, 4-trihydroxybutyl]-1H- quinoxalin-2-one [I] with ethyl chloroacetate gave 1-ethoxycarbonylmethyl-3-[phenylhydrazonon-L-threo-2, 3, 4-trihydroxybutyl]-1H-quinoxalin-2-one [III] and 1-ethoxycarbonylmethyl-3-[5-hydroxymethyl-1-phenylpyrazol-3-y]-1H- quinoxalin-2-one [IV]. Their proportion was dependent upon the conditions of the reaction. Acetylation of compounds III and IV afforded the corresponding acetylated products V and VI, respectively. Periodate oxidation of III gave I- ethoxycarbonylmethyl-3-[1-phenylhydrazono-glyoxal-1-yl]-1H- quinoxalin-2-on [VII]. Condensation of IV with hydrazine hydrate gave 1-hydrazinocarbonylmethyl-3-[5-hydroxmethyl-1-phenylpyrazol-3-yl]-1H- quinoxalin-2-one [VIII], whose reaction with benzaldehyde gave the corresponding hydrazone IX