Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2420-2428.DOI: 10.6023/cjoc201505030 Previous Articles     Next Articles



叶斌a, 莫广珍b,c, 关丽涛d, 吴彦城b, 陈任宏a, 汪朝阳b   

  1. a 广东食品药品职业学院 广州 510520;
    b 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006;
    c 佛山市顺德一中实验学校 顺德 528300;
    d 华南农业大学材料与能源学院 广州 510642
  • 收稿日期:2015-05-18 修回日期:2015-06-27 发布日期:2015-07-08
  • 通讯作者: 陈任宏, 汪朝阳;
  • 基金资助:

    广东省自然科学基金(Nos. 2014A030313429, S2011010001556)、广东省高等学校人才引进专项资金(No. 粤财教[2011]431号)、国家自然科学基金(No. 31200439)、广东食品药品职业学院自然科学研究(No. 2014YZ007)资助项目.

Synthesis of 4-Amino-5-biphenyloxy-3-halo-2(5H)-furanones

Ye Bina, Mo Guangzhenb,c, Guan Litaod, Wu Yanchengb, Chen Renhonga, Wang Zhaoyangb   

  1. a Guangdong Food and Drug Vocational College, Guangzhou 510520;
    b Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry andEnvironment, South China Normal University, Guangzhou 510006;
    c Shunde No. 1 Experimental Middle School, Shunde 528300;
    d College of Materials and Energy, South China Agricultural University, Guangzhou 510642
  • Received:2015-05-18 Revised:2015-06-27 Published:2015-07-08
  • Supported by:

    Project supported by the Natural Science Foundation of Guangdong Province (Nos. 2014A030313429, S2011010001556), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431), the National Natural Science Foundation of China (No. 31200439) and the Natural Science Project of Guangdong Food and Drug Vocational College (No. 2014YZ007).

Two novel 5-biphenyloxy-3,4-dihalo-2(5H)-furanones are synthesized via the direct dehydrative etherification reactions of biphenyl-4-ol with mucochloric acid and mucobromic acid, respectively, using sulfuric acid as a catalyst in toluene at reflux temperature. Taking them as intermediates, the tandem Michael addition-elimination reaction with different representative aliphatic amines is carried out in the presence of KF as a base and catalyst at room temperature. Sixteen 4-amino-5-biphenyloxy-3-halo-2(5H)-furanones are obtained, and the isolated yields are 43%~79% (mostly over 55%). The structures of all newly synthesized compounds were systematically characterized by FTIR, UV, 1H NMR, 13C NMR, MS and elemental analysis. This investigation affords an important novel strategy for the synthesis of different 2(5H)-furanone derivatives having potential bioactivity, especially for the synthesis of 2(5H)-furanones simultaneously with biphenyl and amino structure.

Key words: 2(5H)-furanone, biphenyl structure, synthesis, aliphatic amine, tandem Michael addition-elimination reaction