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

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）.