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4-羟基-3-(2-亚氨基乙基)-2H-苯并吡喃-2-酮类化合物的超声辐射合成

王慧彦1,2*,周丹丹1,陈秭君1   

  1. (1.淮海工学院化学工程学院 连云港 222005；
    2.江苏省有机合成重点实验室， 苏州大学材料与化学化工学部 苏州 215123)
  • 收稿日期:2012-04-01 修回日期:2012-07-10 出版日期:2013-02-10 发布日期:2013-02-10
  • 通讯作者: 王慧彦，讲师; Tel:0518-85862289; E-mail:wanghy0118@163.com; 研究方向：有机合成
  • 基金资助:
    淮海工学院大学生创新实验项目；江苏省普通高校研究生科研创新计划资助项目(CXZZ11_0090)

Synthesis of 4-Hydroxy-3-(2-Imino ethyl)-2H-Chromen-2-One Derivatives under Ultrasound Irradiation

WANG Huiyan1,2*, ZHOU Dandan1, CHEN Zijun1   

  1. (1.Department of Chemical Engineering,Huaihai Institute of Technology,Lianyungang 222005,China;
    2.Key Laboratory of Organic Synthesis of Jiangsu Province,College of Chemistry,
    Chemical Engineering and Materials Science,Soochow University,Suzhou 215123,China)
  • Received:2012-04-01 Revised:2012-07-10 Published:2013-02-10 Online:2013-02-10

PDF

1363

被引次数

4

摘要： 以乙醇为溶剂,4-羟基-3-乙酰基香豆素和胺为原料,对甲苯磺酸为催化剂,在超声波作用下合成一系列4-羟基-3-(2-亚氨基乙基)-2H-苯并吡喃-2-酮类化合物,产率62%~94%。 对产物进行了IR、1H NMR及HRMS表征,对化合物3c进行了X射线衍射分析。 该方法具有反应产率高、时间短、反应条件温和及操作简单等优点。

关键词: Schiff 碱, 羟基乙酰基香豆素, 超声辐射, 合成

Abstract: A series of 4-hydroxy-3-(2-imino ethyl)-2H-chromen-2-ones was first synthesized by the reaction of 4-hydroxy-3-acetyl coumarin and amines in alcohol with 4-methylbenzenesulfonic acid as catalyst under ultrasonic irradiation. The yields were in the range of 62%~94%. The structures of the products were confirmed by IR, 1H NMR and HRMS. The structure of compound 3c was determined by X-ray singlecrystal diffractions. The advantages of this method are high yield, shorter reaction time, mild condition and simple work-up procedures.

Key words: Schiff base, acetyl-hydroxy-2H-chromen-one, ultrasonic irradiation, synthesis

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