合成3,3-二芳基氧化吲哚的新方法  

A Novel Method for The Synthesis of 3,3-Diaryl Quaternary Carbon Oxindoles

作　　者：岳静 何学雯 刘雄利[1] 田民义 YUE Jing;HE Xue-wen;LIU Xiong-li;TIAN Min-yi(Guizhou Medicine Edicine Edible Plant Resources Research and Developmant Center,School of Pharmacy,Guizhou University,Guiyang 550025,China)

机构地区：[1]贵州大学药学院贵州省药食同源植物资源开发工程技术研究中心,贵州贵阳550025

出　　处：《合成化学》2020年第2期153-157,共5页Chinese Journal of Synthetic Chemistry

基　　金：贵州大学培育项目(黔科合平台人才[2018]5781-49号)。

摘　　要：报道了一种合成3,3-二芳基氧化吲哚的新方法。以取代靛红为起始原料,THF为溶剂,在室温下用新制芳基格氏试剂与靛红的3-位羰基发生双芳基化反应,合成了12个未见文献报道的3,3-二芳基氧化吲哚(3a^3l),产率56%~78%,其结构经1H NMR,13C NMR和HR-MS(ESI-TOF)表征。并分析了3a(CCDC:1960434)和3b(CCDC:1960436)的单晶结构。结果表明:3a属triclinic晶系,P-1空间群,晶胞参数a=8.736(2)A,b=8.887(2)A,c=13.862(3)A,α=77.505(18)°,β=72.01(2)°,γ=64.68(2)°;3b属monoclinic晶系,P21/c空间群,晶胞参数a=8.8877(10)A,b=24.734(2)A,c=8.5441(8)A,α=90°,β=113.994(12)°,γ=90°。A new method for the synthesis of 3,3-diaryl oxindoles was reported. Twelve novel 3,3-diaryl oxindoles(3 a^3 l) were synthesized via an biarylation reaction of isatins with aryl Grignard reagents under room temperature conditions in THF for 3 h. The yields were 56%~78%. The structures were characterized by 1H NMR, 13C NMR and HR-MS(ESI-TOF). The single crystal structures of 3 a(CCDC: 1960434) and 3 b(CCDC: 1960436) were confirmed by X-ray. The results indicated that 3 a belong to system triclinic and space group P-1, with cell parameter of a=8.736(2) A, b=8.887(2) A, c=13.862(3) A, α=77.505(18)°, β=72.01(2)°, γ=64.68(2)°;3 b belong to system monoclinic and space group P21/c, with cell parameter of a=8.8877(10) A, b=24.734(2) A, c=8.5441(8) A, α=90°, β=113.994(12)°, γ=90°.

关 键 词：3 3-二芳基氧化吲哚 芳基格氏试剂 靛红 双芳基化反应 合成 晶体结构 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]