摘要
以4-羟基香豆素和邻胺基苯甲醛为原料,高效合成了具有药物活性的3-位邻羟基苯甲酰基单取代的四氢喹啉衍生物.在乙醇溶剂中,反应经过克脑文格尔缩合/[1,5]-氢迁移/环化/水解/脱羧这五个串联过程进行.另外,还实现了底物控制的多样性合成,在无催化剂、无溶剂、室温条件下制备了一系列二香豆素内盐.
The pharmaceutically significant 3-mono-substituted tetrahydroquinoline derivatives carrying ortho-hydroxybenzoyl moiety are constructed via EtOH mediated cascade Knoevenagel condensation/[1,5]-hydride transfer/cyclization/hydrolysis/decarboxylation from 4-hydroxycoumarins and o-aminobenzaldehydes.In addition,the substrate-controlled diverse syntheses also could be achieved,and a variety of the zwitterionic biscoumarin derivatives are facilely provided under catalystand solvent-free conditions at room temperature.
作者
杨晓宇
柳建林
胡方芝
孙红梅
王亮
李帅帅
Yang Xiaoyu;Liu Jianlin;Hu Fangzhi;Sun Hongmei;Wang Liang;Li Shuai-Shuai(College of Chemistry and Pharmaceutical Sciences,Qingdao Agricultural University,Qingdao,Shandong 266109;College of Chemistry and Molecular Engineering,Qingdao University of Science and Technology,Qingdao,Shandong 266042)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2021年第7期2788-2799,共12页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(Nos.21978144,21702117,21776148)
山东省重点研发计划(Nos.2018GSF118224,2019GSF108020,2019RKB01027)
山东省青创科技计划(No.2019KJM002)
青岛科技大学开放基金(Nos.QUSTHX201916,QUSTHX202004)资助项目.
关键词
4-羟基香豆素
氢迁移反应
四氢喹啉
二香豆素内盐
4-hydroxycoumarin
hydride-transfer reaction
tetrahydroquinoline
zwitterionic biscoumarin
