连续双季碳螺环氧化吲哚拼接异噁唑类化合物的合成  

Synthesis of Isoxazole-fused Bispirocyclic Oxindoles Featuring Two Adjacent Spiro Quaternary Stereocentres

作　　者：周豪杰 周韦 田民义 刘雄利[1] 邓国栋[1] ZHOU Hao-jie;ZHOU Wei;TIAN Min-yi;LIU Xiong-li;DENG Guo-dong(National & Local Joint Engineering Research Center for the Exploition of Homology Resources of Medicine and Food, Guizhou University, Guiyang 550025, China)

机构地区：[1]贵州大学西南药食两用资源开发利用技术国家地方联合工程研究中心,贵州贵阳550025

出　　处：《合成化学》2021年第5期418-423,共6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号)。

摘　　要：以硝基异噁唑-3-烯氧化吲哚(1)作为基于给体和受体的3C合成子,与叔丁基酯-3-烯氧化吲哚(2),在碱性催化剂DABCO催化下发生Michael加成环化反应,获得10个新颖的连续双季碳螺环氧化吲哚拼接异噁唑类化合物3a~3j,产率为57%~70%,dr值为4/1~9/1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,并且经过单晶3f进一步确定了其结构。The nitroisoxazole-3-eneindolinones(1)were used as a donor/acceptor-based 3C synthons for the first time.Ten novel isoxazole-fused bispirocyclic oxindoles(3a~3j)were synthesized via Michael addition and then cyclization reaction event of nitroisoxazole-3-eneindolinones 1 with methyleneindolinones(2)under DABCO as catalyst and room temperature conditions.The yields and dr of 3a~3j were 57%~70%and 4/1~9/1,respectively.The structures were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF),and further confirmed by X-ray crystallographic study of single crystal of 3f.

关 键 词：硝基异噁唑-3-烯氧化吲哚 基于给体和受体的3C合成子 Michael加成环化反应 螺环氧化吲哚拼接异噁唑类化合物 合成 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]