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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (08): 1267-1271. 上一篇    下一篇

研究简报

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

程青芳*,a,b ; 许兴友a,b; 王启发c ; 刘丽莎b;
刘望军b; 林 俏b ; 杨绪杰a
  

  1. (a南京理工大学材料化学实验室 南京 210094)
    (b淮海工学院化学工程系 连云港 222005)
    (c淮海工学院江苏省海洋生物技术重点实验室 连云港 222005)
  • 收稿日期:2008-11-12 修回日期:2009-02-06 发布日期:2009-08-30
  • 通讯作者: 程青芳

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

Cheng, Qingfang*,a,b ; Xu, Xingyou a,b; Wang, Qifa c; Liu, Lisha b;
Liu, Wangjunb; Lin, Qiao b; Yang, Xujie a
  

  1. (a Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094) (b Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005) (c Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, Lianyungang 222005)
  • Received:2008-11-12 Revised:2009-02-06 Published:2009-08-30
  • Contact: Cheng, Qingfang

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1471

被引次数

17

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, 1H NMR及单晶解析表征. 该方法具有操作简单和环境友好等优点.

关键词: 3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮, 超声辐射, 一锅合成, 水介质

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-arylmethylene- isoxazol-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 irradia-tion. 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 sin-gle crystal analysis. The work-up procedure is very simple and environmental friendliness.

Key words: ultrasonic irradiation, aqueous media, one-pot synthes, 3-methyl-4-arylmethylene-isoxazol-5(4H)-one