Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (08): 1782-1790.DOI: 10.6023/cjoc201301071 Previous Articles     Next Articles



杨波a, 方向a, 杨雪艳a, 吴范宏b   

  1. 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:2013-01-27 修回日期:2013-03-20 发布日期:2013-04-08
  • 通讯作者: 杨雪艳, 吴范宏;
  • 基金资助:

    国家自然科学基金(Nos. 20972050, 21172148)资助项目.

A Convenient Synthesis of 5-Fluoroalkyloxazoline

Yang Boa, Fang Xianga, Yang Xueyana, Wu Fanhongb   

  1. 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 201418
  • Received:2013-01-27 Revised:2013-03-20 Published:2013-04-08
  • Supported by:

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

An efficient and convenient protocol for the synthesis of 5-fluoroalkyl-2-oxazoline is described. The 1-allyl-3-arylurea was synthesized by the reaction of isocyanate with allyl amine in methylene chloride at room temperature. The reaction of 1-allyl-3-arylurea with fluoroalky iodide initiated by sodium dithionite in aqueous acetonitrile resulted in adducts that undergoes a cyclization in water or DMF to form 5-fluoroalkyloxazoline with moderate yields. It was also found that the products can be more efficiently formed via an AIBN-initiated, one-pot addition-cyclization sequence from 1-allyl-3-arylurea with fluoroalkyl iodide.

Key words: oxazoline, fluorinated alkyl, O-cyclization, free radical reaction