TMSCl促进的分子内亲核取代反应合成α-亚烷基-哌啶酮

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，13C NMR和HR-MS（ESI）确证。在最优反应条件（12 mmol， n-BuLi 2．4 mmol， TMSCl 3 mmol， THF 20 mL，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 nucleophilic substitution promoted by chlorotrimethylsilane , using vinyl iodides as precursors , n-BuLi as lithiating reagent , and THF as solvent .The structures were confirmed by 1 H NMR, 13 C 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, TMSCl 3 mmol, THF 20 mL, reaction at 170 ℃for 1 h).