Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 104-112.DOI: 10.6023/cjoc1106302 Previous Articles     Next Articles



傅建花, 汪朝阳, 霍景沛, 谭越河, 曾荣华   

  1. 华南师范大学化学与环境学院 广州 510006
  • 收稿日期:2011-06-30 修回日期:2011-08-29 发布日期:2011-09-21
  • 通讯作者: 汪朝阳
  • 基金资助:

    国家自然科学基金(No. 20772035)、广东省自然科学基金(No. 5300082)及广东省高等学校人才引进专项基金(No. [2011]431)资助项目.

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

Fu Jianhua, Wang Zhaoyang, Huo Jingpei, Tan Yuehe, Zeng Ronghua   

  1. School of Chemistry and Environment, South China Normal University, Guangzhou 510006
  • Received:2011-06-30 Revised:2011-08-29 Published:2011-09-21
  • Contact: Zhaoyang Wang
  • Supported by:

    Project supported by the the National Natural Science Foundation of China (No. 20772035), the Natural Science of Foundation of Guangdong Provine (No. 5300082) and the 3rd Talents Special Funds of Guangdong Higher Education (No. [2011]431).

Using KF as catalyst and tetrahydrofuran as solvent, 5-alkyloxy-3,4-dihalo-2(5H)-furanones was reacted with several aliphatic amines. The chemical structures and absolute configurations of the products were confirmed via rotation, UV-Vis, IR, 1H NMR, 13C NMR, MS techniques, elemental analysis and X-ray single crystal diffraction. Thirteen new normal products β-amino-2(5H)-furanones were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases. However, the reaction between the larger steric dicyclohexyl amine and 5-alkyloxy-3,4-dihalo-2(5H)-furanones yielded four new abnormal products, (E)-alkyl 2-halo-4-dicyclohexylamino-4-oxobut-2-enoate. The possible mechanism for the formation of 2(5H)-furanone ring-opening products involving in the rearrangement reaction was proposed.

Key words: 5-alkoxy-3,4-dihalo-2(5H)-furanone, aliphatic saturated secondary amine, tandem Michael addition-elinmination reaction, β-amino-2(5H)-furanone, ring-opening rearrangement reaction