Studies in isoxazole chemistry. II. Isoxazoles from the Δ<sup>2</sup>-isoxazolin-5-ols and their acetates
作者:R. G. Micetich
DOI:10.1139/v70-075
日期:1970.2.1
Various 3-substituted-5-acetoxy-Δ2-isoxazolines were made by the 1,3-dipolar cycloaddition of nitrile oxides to vinyl acetate or isopropenyl acetate. These compounds were readily converted in high yield to 3-substituted isoxazoles or 3-substituted-5-methylisoxazoles respectively, on heating. Treatment of the 3-substituted-5-acetoxy-Δ2-isoxazolines with sodium hydroxide in methanol gave rise to the
通过腈氧化物与乙酸乙烯酯或乙酸异丙烯酯的 1,3-偶极环加成反应制备了各种 3-取代-5-乙酰氧基-Δ2-异恶唑啉。这些化合物在加热时很容易以高产率分别转化为 3-取代的异恶唑或 3-取代的 5-甲基异恶唑。在甲醇中用氢氧化钠处理 3-取代-5-乙酰氧基-Δ2-异恶唑啉在酸化后产生稳定的 Δ2-异恶唑啉-5-醇。这些化合物也可以通过单独加热或在亚硫酰氯的存在下更好地转化为 3-取代的异恶唑。讨论了这些化合物的核磁共振谱。