摘要
报道了一类新型的微波辅助对甲基苯磺酸促进的[3+3]环化反应.利用烯胺酮或烯胺内酯可作为1,3-双亲核试剂及炔丙醇可作为1,3-双亲电试剂的特性,使其在微波辐射及对甲苯磺酸促进条件下于冰醋酸中在70℃反应,实现了[3+3]环化反应,分别区域选择性地合成了2,2-二芳基取代四氢喹啉-5(1H)-酮衍生物和2,2-二芳基取代二氢呋喃并[3,4-b]吡啶-5-酮衍生物,产率良好.该反应利用微波合成技术促使反应,在短时间内完成(30 min),唯一副产物为水.此外,该方法具有原料简单易得、操作简单及底物普适性广等优点,从而为具有潜在应用价值的稠合吡啶骨架的构建提供了一种绿色、经济且高效的合成策略,符合绿色化学理念.
A new microwave-assisted p-TsOH-promoted[3+3]cyclization was developed.By using the characteristics of enaminones or enamino lactones as 1,3-dinucleaphilic reagents and propargyl alcohols as 1,3-electrophilic reagents,p-TsOH-promoted[3+3]cyclization of these substrates at 70℃was carried out in acetic acid under microwave irradiation,regioselectively affording 2,2-diaryl-substituted tetrahydroquinoline-5(1H)-ones and 2,2-diaryl-substituted dihydrofuro[3,4-b]pyridin-5-ones in good yields.The reaction can be completed within a short period(30 min)by microwave synthetic technology,in which water was the sole by-product.This method features simple and available starting materials,simple operation and wide substrate scope,and provides a green,economic,and efficient synthetic strategy for the construction of fused pyridine skeleton with potential application,which is consistent with the concept of green chemistry.
作者
吴亚男
杜建宇
郝文娟
姜波
Yanan Wu;Jianyu Du;Wenjuan Hao;Bo Jiang(School of Chemistry and Chemical Engineering,Nantong University,Nantong,Jiangsu 226019;School of Chemistry&Materials Science,Jiangsu Normal University,Xuzhou,Jiangsu 221116)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2021年第4期1563-1571,共9页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.21971090)
江苏省品牌专业基金资助项目。
