FeCl3催化4-羟基香豆素烷基化衍生物的合成  

Synthesis of 4-Hydroxycoumarin Derivatives by FeCl3-catalyzed Alkylation

作　　者：陈怡心 王治明 王钰蓉[1] CHEN Yi-xin;WANG Zhi-ming;WANG Yu-rong(Collegel of Pharmaceutical science,Zhejiang Chinese Medical University,Hangzhou 311400,China;School of Advanced Study,Taizhou University,Taizhou 318000,China)

机构地区：[1]浙江中医药大学药学院,浙江杭州311400 [2]台州学院高等研究院,浙江台州318000

出　　处：《合成化学》2019年第12期971-977,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21372033)

摘　　要：以4-羟基香豆素、查尔醇(或苄醇)为原料,FeCl 3作催化剂,1,2-二氯乙烷作溶剂,在室温下实现了4-羟基香豆素的烷基化反应,高效合成了10个4-羟基香豆素的烷基化衍生物(3a^3e,5a^5e),收率70%~91%和67%~78%。在此基础上,利用FeCl 3/DDQ催化体系的一锅法串联环化反应合成了一系列2,4-二芳基-2 H,5 H-吡喃并[3,2-c]苯并吡喃-5-酮衍生物(6a^6d),收率52%~85%。其中3b,3d,3e,6b,6c,6d为新化合物,其结构经1 H NMR,13 C NMR和HR-MS(ESI)表征。Ten 4-hydroxycoumarin derivatives(3a^3e,5a^5e)with the yield of 70%~91%and 67%~78%,were synthesized by alkylation reaction of 4-hydroxycoumarin with charol(or benzyl alcohols)at room temperature in 1,2-dichloroethane,using FeCl 3 as the catalyst.Based on the former alkylation,2,4-diaryl-2 H,5 H-pyrano[3,2-c]-chromen-5(2 H)-one derivatives(6a^6d)were synthesized by one-pot tandem cyclization in FeCl 3/DDQ catalytic system with yield of 52%~85%.Among them,3b,3d,3e,6b,6c and 6d were novel compounds.The structures were characterized by 1 H NMR,13 C NMR and HR-MS(ESI).

关 键 词：查尔醇 苄醇 4-羟基香豆素 烷基化 一锅法 合成 

分 类 号：O625.34[理学—有机化学]