摘要
设计并合成了新型离子液体负载的手性硫代咪唑啉酮,以L-苯丙氨酸为手性原料,依次经过Boc保护、酰胺化反应、脱Boc反应和环化反应制备了(S)-5-苄基-2,2-二甲基-3-(1-咪唑基丙基)-4-氧咪唑烷酮,进一步经Lawesson试剂硫代,在甲苯溶剂中80℃下反应8h,得到的手性硫代咪唑啉酮再与正丁基碘在乙腈溶液中回流反应24h,首次制得了新型离子液体负载的手性硫代咪唑啉酮,并取得了较佳的立体选择性.其中,实验通过对脱Boc反应进行改进,即采用氯化氢的二氧六环溶液为反应试剂进行脱Boc反应,优化反应条件,获得了较佳的收率.
A novel synthesis method of（S）-type ionic liquid immobilized imidazolethinones was reported in this paper.（S）-3-（3-（1H-Imidazol-1-yl）propyl）-5-benzyl-2,2-dimethylimidazolidin-4-one was synthesized from L-phenylalanine via Boc-protection,amidation,Boc-deprotection,cyclization.Then it was followed the sulfurated reaction with using Lawesson reagent as sulfuration agent in toluene at 80 ℃for 8hrs to give the chiral imidazolethinone in high ee value.The reaction of the obtained imidazolethione with n-iodobutane produced the（S）-type ionic liquid immobilized imidazolethinone.The Boc-deprotection product was obtained in quantitative yield by using the HCl/1,4-dioxane as reaction reagents.
出处
《浙江工业大学学报》
CAS
北大核心
2016年第5期510-514,共5页
Journal of Zhejiang University of Technology
基金
国家自然科学基金资助项目(21206148)
作者简介
梁现蕊（1975-），女，山东临沂人，副教授，博士，研究方向为手性合成及药物分析，Email：liangxrvicky@zjut．edu．cn．
