新型3-烯色满酮拼接季碳氧化吲哚类化合物的合成  

Synthesis of 3-Alkenylchromanone-fused Quaternary Oxindoles

作　　者：谢丹[1] 陈子月 朱君 韩晓雪 张敏[1] 刘雄利[1] 邓国栋[1] XIE Dan;CHEN Ziyue;ZHU Jun;HAN Xiaoxue;ZHANG Min;LIU Xiongli;DENG Guodong(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》2022年第4期305-310,共6页Chinese Journal of Synthetic Chemistry

基　　金：贵大培育项目(202052,202078)。

摘　　要：以色酮取代氧化吲哚(1)为原料,在有机碱DABCO的催化作用下,进攻3-烯色满酮2的烯键,发生Michael加成反应,然后脱除OBoc基团生成烯键,合成了9个未见文献报道的3-烯色满酮拼接季碳氧化吲哚类化合物(3a~3i),产率60%~87%,dr值为2:1~5:1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,并通过单晶培养确定了化合物3f的相对构型。该类化合物含有色酮、色满酮和氧化吲哚等3个具有潜在生物活性的骨架,在医药行业具有潜在应用价值。In this paper,chromone-substituted oxindoles 1 were used as raw materials.Under the catalysis of organic base DABCO,the alkene bond of 3-alkenylchromanones 2 was attacked,Michael addition reaction occurred,and then OBOC group was removed to form alkene bond.Nine 3-alkenylchromanone-fused quaternary oxindoles 3a~3i were obtained.The yields and dr of 3a~3i were 60%~87%and 2:1~5:1,respectively.The structures of products 3 were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The relative configuration of compound 3f was further determined by single crystals.These compounds contain three potential bioactive skeletons:chromone,chromanone and oxindole,which have important potential value for the pharmaceutical industry.

关 键 词：色满酮 季碳氧化吲哚 MICHAEL加成反应 三乙烯二胺 3-烯色满酮拼接季碳氧化吲哚 合成 相对构型 

分 类 号：O626.13[理学—有机化学] O623.7[理学—化学]