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2013 , Vol. 33 >Issue 05: 1088 - 1095

DOI: https://doi.org/10.6023/cjoc201210034

研究简报

一种有效合成3-芳基-4-氟烷基-2-噁唑烷酮的方法

  • 杨波 ,
  • 赵敏 ,
  • 方向 ,
  • 杨雪艳 ,
  • 吴范宏
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  • a 华东理工大学化学与分子工程学院 上海 200237;
    b 上海应用技术学院化学与环境工程学院 上海 201418

收稿日期: 2012-10-18

  修回日期: 2013-01-21

  网络出版日期: 2013-01-25

基金资助

国家自然科学基金(Nos. 20972050, 21172148).

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A Convenient Synthesis of 3-Aryl-4-fluoroalkyl-2-oxazolidinone

  • Yang Bo ,
  • Zhao Min ,
  • Fang Xiang ,
  • Yang Xueyan ,
  • Wu Fanhong
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  • a School of Chemistry and Molecular Enineering, School of Chemistry and Molecular Enineering, East China University of Science and Technology, Shanghai 200237;
    b School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235

Received date: 2012-10-18

  Revised date: 2013-01-21

  Online published: 2013-01-25

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20972050, 21172148).

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摘要

报道了一种方便有效地合成3-芳基-4-氟烷基-2-噁唑烷酮的方法. 用芳基胺作为起始原料通过与氯甲酸烯丙基酯反应以95.8%～99.5%的收率得到芳基氨基甲酸烯丙基酯. 芳基氨基甲酸烯丙基酯与氟烷基碘在乙腈和水的混合液中由连二亚硫酸钠引发在室温下发生自由基加成反应得到氟烷基化的加成产物. 加成产物在碱性条件下发生分子内的N-环合反应得到3-芳基-4-氟烷基-2-噁唑烷酮. 整个反应都在室温下进行, 并且没有用到光气合成了3-芳基-4-氟烷基- 2-噁唑烷酮, 该方法具有原料易得, 条件温和, 绿色环保的优点.

关键词： 2-噁唑烷酮; 氟烷基化; 合成; N-环合

本文引用格式

杨波 , 赵敏 , 方向 , 杨雪艳 , 吴范宏 . 一种有效合成3-芳基-4-氟烷基-2-噁唑烷酮的方法[J]. 有机化学, 2013 , 33(05) : 1088 -1095 . DOI: 10.6023/cjoc201210034

Abstract

An efficient and convenient protocol for the synthesis of 3-aryl-4-fluoroalkyl-2-oxazolidinones is described. The allyl arylcarbamates were obtained from the corresponding aromatic amine and chloroformate allyl ester in high yields. The reaction of allyl arylcarbamates with fluoroalkyl iodide initiated by sodium dithionite in aqueous acetonitrile afforded adducts, which underwent cyclization in the presence of sodium hydride to give corresponding 3-aryl-4-fluoroalkyl-2-oxazolidinone in middle yield. All reactions were carried out in room temperature without phosgene to obtain 3-aryl-4-fluoroalkyl- 2-oxazolidinone. The advantages of this method are that the raw material is easy to get, the operation is simple, it is green and environmental-protection.

Key words： oxazolidin-2-ones; fluorinated alkyl; synthesis; N-cyclizaion

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