铜催化对亚甲基苯醌/偶氮试剂/水三组分反应合成苯并呋喃-2-酮类化合物  

Copper-Catalyzed Three-Component Synthesis of Benzofuran-2-one from para-Quinone Methides/Azo Reagent/H2O

作　　者：盛回香 余健 王硕文[1] 徐振华 唐石[1] SHENG Huixiang;YU Jian;WANG Shuowen;XU Zhenhua;TANG Shi(Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wuling ountains,College of Chemistry and Chemical Engineering Jishou University,Hunan,Jishou 416000,China)

机构地区：[1]吉首大学化学化工学院武陵山民族药解析与创制湖南省工程实验室

出　　处：《应用化学》2019年第11期1266-1274,共9页Chinese Journal of Applied Chemistry

基　　金：国家自然基金(21462017);吉首大学湖南省大学生研究性学习和创新性实验项目(JGCX2018149)资助~~

摘　　要：发展了一种高效、简便的潜在生物活性的含氰苯并呋喃-2-酮类化合物的合成新方法。以廉价碘化亚酮为催化剂,锌粉为添加剂,催化对亚甲基苯醌与1,1-偶氮双(环己烷甲腈)和H 2 O三组分反应,经历1,6-共轭加成/芳构化,惰性碳-碳键断裂,以及后续的串联自由基插氰/环化及水解等步骤,“一锅法”快速合成了一系列含氰苯并呋喃酮结构的化合物。为含氰苯并呋喃酮类化合物的合成提供一条简便而高效的途径,同时也为对亚甲基苯醌类化合物的高值化应用提供一个新的思路。A new and efficient method for the synthesis of potentially biologically active cyano-containing benzofuran-2-one derivatives has been developed.In the presence of low-cost CuI and zinc powder,the three-component reactions of para-quinone methides with 1,1-azobis(cyclohexanecarbonitrile)and H 2 O proceed smoothly through radical cascades,including 1,6-conjugate addition/aromatization,inert C(aryl)—C(t-butyl)bond cleavage and downstream cyano-insertion/cyclization/hydrolysis,which leads to a series of cyano-containing benzofuran-2-ones.This method offers a simple and efficient way for the synthesis of cyano-containing benzofuranone derivatives,as well as a new idea for the high-value application of para-quinone methides.

关 键 词：C—C键官能化 1 1-偶氮双(环己烷甲腈) 铜催化 苯并呋喃酮 对亚甲基苯醌 

分 类 号：O622.6[理学—有机化学]