超声辐射下水介质中一锅合成3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮

One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones in Aqueous Media under Ultrasonic Irradiation

报道了室温超声辐射下,水相中通过乙酰乙酸甲酯、盐酸羟胺和芳香醛的三组分一锅反应,合成了一系列3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮衍生物.在超声波辐射下,参与反应的醛无论芳环上连有吸电子基或供电子基,该一锅反应在室温下都能较好地进行;对于α,β-不饱和醛、杂环芳醛以及二元芳醛与乙酰乙酸甲酯、盐酸羟胺的一锅反应也能在室温下顺利进行,获得中等以上的收率.产物的结构通过元素分析,IR,1HNMR及单晶解析表征.该方法具有操作简单和环境友好等优点.

One-pot three component condensation reactions of methyl acetoacetate, hydroxylamine hydrochloride and aromatic aldehydes were used for the preparation of a series of 3-methyl-4-arylmethyleneisoxazol-5（4H）-one derivatives under ultrasonic irradiation in aqueous media at room temperature. The third component may be aldehydes bearing electron-doner or electron-drawing groups, the one-pot condensation has been found to proceed efficiently at room temperature in good to medium yields under ultrasonic irradiation. The condensation of methyl acetoacetate, hydroxylamine hydrochloride with α,β-unsaturated, hetero aromatic aldehydes as well as p-phthalaldehyde also proceeded smoothly at room temperature in medium yields. The structures of the products were characterized by elemental analysis, IR, 1H NMR, and X-ray single crystal analysis. The work-up procedure is very simple and environmental friendliness.