4,5位置換イソオキサゾール類の合成及び開裂反応に関する研究 (第1報)

抄録

Ten kinds of R-COCH₂-R′(R=phenyl, p-tolyl, anisyl, α-naphthyl, β-naphthyl, R′=methyl, ethyl, phenyl) was formylated with ethyl formate by the usual procedure to form α-formyl-ketone (I) and application of hydroxylamine hydrochloride to (I) in ethanol afforded isoxazole compounds (II) instead of oxime or dioxime of (I). Application of sodium ethoxide to (II) effected cleavage to form α-cyano-ketone (III) whose hydrolysis with dilute alkali hydroxide resulted in the formation of R-COOH and R′-CH₂CN. This proved that (II) is a 4, 5-disubstituted isoxazole with R′ in 4- and R in 5-position. This process seemed to be applicable as a general procedure for synthesis and detection of 4, 5-disubstituted isoxazoles.