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

doi:10.6023/cjoc201505030

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

Notes

3-卤-4-脂肪胺基-5-联苯氧基-2(5H)-呋喃酮的合成

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

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 E-mail:chenrh@gdyzy.edu.cn;wangzy@scnu.edu.cn
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 Bin^a, Mo Guangzhen^b,c, Guan Litao^d, Wu Yancheng^b, Chen Renhong^a, Wang Zhaoyang^b

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).

1. Synthesis of 4-Amino-5-biphenyloxy-3-halo-2(5H)-furanones.PDF(1613KB)

Abstract

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

Cite this article

Ye Bin, Mo Guangzhen, Guan Litao, Wu Yancheng, Chen Renhong, Wang Zhaoyang. Synthesis of 4-Amino-5-biphenyloxy-3-halo-2(5H)-furanones[J]. Chin. J. Org. Chem., 2015, 35(11): 2420-2428.

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3-卤-4-脂肪胺基-5-联苯氧基-2(5H)-呋喃酮的合成

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

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