氮杂环卡宾(NHC)催化[3+2]环加成反应高非对映选择性地构建螺氧吲哚二氢呋喃稠合吡唑啉酮化合物  

N-Heterocyclic Carbene(NHC)-Catalyzed[3+2]Cycloaddition to Highly Diastereoselective Synthesis of Spirooxindole Dihydrofuran Fused Pyrazolone Compounds

作　　者：刘岩[1] 王晓梅 何林[1] 李师伍 赵志飞 Liu Yan;Wang Xiaomei;He Lin;Li Shiwu;Zhao Zhifei(State Key Laboratory Incubation Base for Green Processing of Chemical Engineering,School School of Chemistry and Chemical Engineering,Shihezi University,Shihezi,Xinjiang 832000)

机构地区：[1]石河子大学化学化工学院、化工绿色过程省部共建国家重点实验室培育基地,新疆石河子832000

出　　处：《有机化学》2024年第4期1301-1310,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.22101188);石河子大学(Nos.2022ZK003,RCZK202001)资助项目。

摘　　要：在氮杂环卡宾(NHC)催化下,靛红衍生的烯醛与吡唑啉酮4,5-二酮化合物经[3+2]环加成反应高效生成含连续两个螺中心的螺氧吲哚二氢呋喃稠合吡唑啉酮化合物.该反应具有很好的底物普适性,获得了中等到优异的产率(41%~99%)和一般到优良的非对映选择性(2∶1~>20∶1 dr).此外,反应还具有反应条件温和及操作简便的优点,并且克级反应也能顺利进行.该研究为高效构建官能团化的螺氧吲哚二氢呋喃稠合吡唑啉酮化合物提供了新的合成方法学.An efficient N-heterocyclic carbene(NHC)-catalyzed[3+2]cycloaddition of isatin-derived enal and pyrazole-4,5-diones to directly synthesis of spirooxindole dihydrofuran fused pyrazolone compounds containing two vicinal spirocenters was disclosed.This approach was qualified with broad substrate scope,achieving moderate to excellent yield(41%~99%)and general to excellent diastereoselective(2∶1~>20∶1 dr).Furthermore,the reaction has the advantages of mild reaction conditions and easy operation,and the gram scale reaction can also proceed smoothly.This study provides a new synthetic methodology for the efficient construction of multi-functionalized spirooxindole dihydrofuran fused pyrazolone compounds.

关 键 词：氮杂环卡宾 环加成 螺环氧化吲哚 吡唑啉酮 

分 类 号：O621.251[理学—有机化学] O626[理学—化学]