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.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
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~~
