TMSCl促进的分子内亲核取代反应合成α-亚烷基-哌啶酮  

Synthesis of 3-Alkylidene-piperidin-4-ones via Intramolecular Nucleophilic Substitution Promoted by TMSCl

作　　者：钟铮[1] 密霞 秦树艳 冯卫生[1] 孙德梅[1] 

机构地区：[1]河南中医药大学药学院,河南郑州450046

出　　处：《合成化学》2016年第7期609-611,共3页Chinese Journal of Synthetic Chemistry

摘　　要：以烯基碘代物为底物,丁基锂为锂代试剂,THF为溶剂,在TMSCl促进下通过分子内亲核取代反应合成了4个α-亚烷基-哌啶酮(2a^2d),其结构经~1H NMR,^(13)C NMR和HR-MS(ESI)确证。在最优反应条件(1 2 mmol,n-Bu Li 2.4 mmol,TMSCl 3 mmol,THF 20 m L,于170℃反应1 h)下,2a^2d收率68%~84%。Four 3-alkylidene-piperidin-4-one analogues （2a - 2d） were synthesized by intramolecular nueleophilic substitution promoted by ehlorotrimethylsilane, using vinyl iodides as precursors, n-BuLi as lithiating reagent, and THF as solvent. The structures were confirmed by 1H NMR, -3C NMR and HR-MS（ESI）. The yields of 2a - 2d were 68% - 84% under the optimized reaction conditions （1 2 mmol, n-BuLi 2.4 mmol, TMSC1 3 mmol, THF 20 mL, reaction at 170 ℃ for 1 h）.

关 键 词：α-亚烷基-哌啶酮 分子内亲核取代反应 三甲基氯硅烷 合成 

分 类 号：O621.3[理学—有机化学]