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

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.