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3-卤-4-脂肪胺基-5-联苯氧基-2(5H)-呋喃酮的合成 被引量:1

Synthesis of 4-Amino-5-biphenyloxy-3-halo-2(5H)-furanones
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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.
作者 叶斌 莫广珍 关丽涛 吴彦城 陈任宏 汪朝阳 Ye Bin;Mo Guangzhen;Guan Litao;Wu Yancheng;Chen Renhong;Wang Zhaoyang; (a Guangdong Food and Drug Vocational College, Guangzhou 510520) (b Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, 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)
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
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 2(5H)-furanone biphenyl structure synthesis aliphatic amine tandem Michael addition-elimination reaction
作者简介 E-mail: chenrh@gdyzy.edu.cn E-mail: wangzy@scnu.edu.cn
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