Reaction of N-hydroxyacetoacetanilide with carbonyl reagents.
作者:KATSUMI TABEI、ETSUKO KAWASHIMA、TETSUZO KATO
DOI:10.1248/cpb.29.244
日期:——
The reaction of N-hydroxyacetoacetanilide derivatives (1a-g) with hydroxylamine in aqueous ethanol gave 3-methyl-4-arylhydrazono-5-isoxazolones (3a-g). When ethanol or chloroform was used as the reaction medium, the reaction of N-hydroxyacetoacetanilide (1a) with carbonyl reagents gave N-phenylhydroxylamine derivatives and five-membered heterocycles such as 3-methyl-5-isoxazolone or 3-methyl-5-pyrazolone derivatives. The mechanism of the formation of these products is discussed.
在乙醇水溶液中,N-羟基乙酰乙酰苯胺衍生物(1a-g)与羟胺反应生成 3-甲基-4-芳基肼基-5-异恶唑酮(3a-g)。当使用乙醇或氯仿作为反应介质时,N-羟基乙酰乙酰苯胺(1a)与羰基试剂反应生成 N-苯基羟胺衍生物和五元杂环,如 3-甲基-5-异恶唑酮或 3-甲基-5-吡唑酮衍生物。本文讨论了这些产物的形成机理。