3-卤-4-脂肪胺基-5-联苯氧基-2(5H)-呋喃酮的合成
收稿日期: 2015-05-18
修回日期: 2015-06-27
网络出版日期: 2015-07-08
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
Received date: 2015-05-18
Revised date: 2015-06-27
Online 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).
以硫酸为催化剂, 4-羟基联苯与粘卤酸在甲苯溶剂中回流, 经脱水醚化反应合成了3,4-二卤-5-联苯氧基-2(5H)-呋喃酮化合物. 以这2个新型的中间体与不同的代表性脂肪胺类在KF催化的室温条件下, 通过串联的迈克尔加成-消除反应, 得到了16个新的3-卤-4-脂肪胺基-5-联苯氧基-2(5H)呋喃酮化合物, 产率43%～79%(大部分55%以上). 新化合物的结构经FTIR、UV、1H NMR、13C NMR、MS和元素分析确证.
关键词： 2(5H)-呋喃酮; 联苯结构; 合成; 脂肪胺; 串联迈克尔加成-消除反应
叶斌 , 莫广珍 , 关丽涛 , 吴彦城 , 陈任宏 , 汪朝阳 . 3-卤-4-脂肪胺基-5-联苯氧基-2(5H)-呋喃酮的合成[J]. 有机化学, 2015 , 35(11) : 2420 -2428 . DOI: 10.6023/cjoc201505030
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.
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