8-三甲基硅乙炔基-6-吡啶-2-基-4 H-苯并[f]咪唑并[1,5-a][1,4]二氮杂-3-羧酸乙酯的合成  

Synthesis of 8-Trimethylsilyacetylenyl-6-pyridin-2-yl-4 H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic Acid Ethyl Ester

作　　者：杨洁[1,2,3] 宋玉凯[1] 舒仕维 王梁 刘晓霞 YANG Jie;SONG Yu-kai;SHU Shi-wei;WANG Liang;LIU Xiao-xia(College of Life Science and Chemistry,Wuhan Donghu University,Wuhan,430212,China;Innovation Institute for Biomedical Materials,Wuhan Donghu University,Wuhan 430212,China;College of Life Science and Technology,Huazhong University of Science and Technology,Wuhan 430074,China)

机构地区：[1]武汉东湖学院生命科学与化学学院,湖北武汉430212 [2]武汉东湖学院生物医用材料创新研究所,湖北武汉430212 [3]华中科技大学生命科学与技术学院,湖北武汉430074

出　　处：《合成化学》2021年第10期862-866,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家级大学生创新创业训练计划项目(202011798001);湖北省自然科学基金资助项目(2017CFB732);湖北省教育厅科研计划项目(B2021294)。

摘　　要：报道了GABA A受体的α2/α3选择性配体(HZ-166)的关键中间体8-三甲基硅乙炔基-6-吡啶-2-基-4 H-苯并[f]咪唑并[1,5-a][1,4]二氮杂-3-羧酸乙酯(HZ-165)的一种合成方法。该方法以4-溴-2-(2′-吡啶基羰基)苯胺为原料,经亲核加成、关环反应、Vilsmeier-Haack反应和Sonogashira反应合成得到目标产物,产物结构经^(1)H NMR和MS(ESI)确证.A synthetic method of 8-trimethylsilyacetylenyl-6-pyridin-2-yl-4 H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid ethyl ester(HZ-165),which is the key intermediate of theα2/α3 selective ligand(HZ-166)of GABA_( A )receptor,was developed.The target product was synthesized from 4-bromo-2-(2′-pyridylcarbonyl)aniline by nucleophilic reaction,cyclization,Vilsmeier-Haack reaction,and Sonogashira reaction.The reaction of each step was monitored by thin layer chromatography(TLC).The structures of the products were confirmed by ^(1)H NMR and MS(ESI).

关 键 词：镇痛药 中间体 合成 选择性配体 Vilsmeier-Haack反应 SONOGASHIRA反应 咪唑 

分 类 号：O626[理学—有机化学] R914.5[理学—化学]