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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 01: 95 - 103

DOI: https://doi.org/10.6023/cjoc1107142

Articles

Researches on the Reaction of 5-Alkoxy-3,4-dihalo-2(5H)-furanones with Unsaturated Amines

  • CHEN Ren-Hong ,
  • FU Jian-Hua ,
  • LI Guo-Liang ,
  • TAN Yue-He ,
  • WANG Chao-Yang ,
  • YUAN Ping
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  • a Guangdong Food and Drug Vocational College, Guangzhou 510520;
    b School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2011-07-14

  Revised date: 2011-09-02

  Online published: 2011-09-26

Supported by

Project supported by National Natural Science Foundation of China (No. 20772035), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (Nos. 5300082, S2011010001556).

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Abstract

In order to further explore the reactions of 5-alkoxy-3,4-dihalo-2(5H)-furanone with amines, the reactions with a series of unsaturated amines were investigated using KF as catalyst and THF as solvent. Sixteen new β-amino-2(5H)-furanone products were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases, and their chemical structures and absolute configurations were confirmed via rotation, UV-Vis, IR, 1H NMR, 13C NMR, MS, elemental analysis and X-ray single crystal diffraction. However, the reaction between 2,5-dimethyl-3-pyrroline and 5-menthoxy-3,4-dihalo- 2(5H)-furanones with larger steric hindrance just yielded unexpected 2(5H)-furanone ring-opening products, while 5-methoxy-3,4-dihalo-2(5H)-furanones with smaller steric hindrance gave both expected β-amino-2(5H)-furanones and unexpected isomers involving the ring-opening rearrangement mechanism. The latter indicated that the steric hindrance of substrates could affect the reactions and even cause competitive reaction.

Key words： 5-alkoxy-3,4-dihalo-2(5H)-furanone; unsaturated amine; tandem Michael addition-elimination reaction; β-amino-2(5H)-furanone; ring-opening rearrangement reaction; steric hindrance; competitive reaction

Cite this article

CHEN Ren-Hong , FU Jian-Hua , LI Guo-Liang , TAN Yue-He , WANG Chao-Yang , YUAN Ping . Researches on the Reaction of 5-Alkoxy-3,4-dihalo-2(5H)-furanones with Unsaturated Amines[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 95 -103 . DOI: 10.6023/cjoc1107142

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