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

作　　者：叶斌[1] 莫广珍[2,3] 关丽涛[4] 吴彦城 陈任宏[1] 汪朝阳[2] 

机构地区：[1]广东食品药品职业学院,广州510520 [2]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 [3]佛山市顺德一中实验学校,顺德528300 [4]华南农业大学材料与能源学院,广州510642

出　　处：《有机化学》2015年第11期2420-2428,共9页Chinese Journal of Organic Chemistry

基　　金：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~~

摘　　要：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、^(13)CNMR、MS和元素分析确证.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, 13 C 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.

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 

分 类 号：O626[理学—有机化学]