邻亚甲醌与硫叶立德反应合成2,3-二取代苯并二氢呋喃化合物  

Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides

作　　者：李梦竹 孟博莹 兰文捷 傅滨[1] Li Mengzhu;Meng Boying;Lan Wenjie;Fu Bin(College of Science,China Agricultural University,Beijing 100193)

机构地区：[1]中国农业大学理学院,北京100193

出　　处：《有机化学》2024年第1期195-203,共9页Chinese Journal of Organic Chemistry

基　　金：国家重点研发计划(No.2017YFD0200301)资助项目.

摘　　要：发展了一种简便有效的通过邻甲亚醌与硫叶立德反应合成苯并二氢呋喃化合物的方法.在二氯甲烷中和二异丙基乙基胺存在下,反应能够在室温下1 h内完成,以良好至优秀的收率得到反式-2,3-二取代二氢苯并呋喃产物.反应能够扩大到克级规模,产物能够转化为潜在生物活性的苯并呋喃衍生物,并推测了可能的反应机理.A facile and efficient approach to dihydrobenzofurans from sulfur ylides and o-quinone methides(o-QMs)was developed.In most cases,the reaction could be completed in the presence of N,N-diisopropylethylamine(DIPEA)in CH2Cl2 at room temperature within 1 h,providing trans-2,3-disubstitiuted dihydrobenzofurans in good to excellent yields.The reaction could expand to a scale of grams,and the products could be converted into the potentially bioactive benzofuran derivatives.The plausible mechanism is proposed.

关 键 词：苯并二氢呋喃 邻亚甲醌 硫叶立德 [4+1]环加成 碱催化 

分 类 号：O626.11[理学—有机化学]