3,5,6-三甲基-哌嗪-2-甲醛的合成研究  

Synthesis of 3,5,6-trimethylpyrazine-2-carbaldehyde

作　　者：徐小娜 张婧 王晓霞[1] 孙艺方[1] 仝红娟 朱周静 XU Xiao-na;ZHANG Jing;WANG Xiao-xia;SUN Yi-fang;TONG Hong-juan;ZHU Zhou-jing(School of Pharmaceutical&Chemical Engineering,Xianyang Vocational Technical College,Xianyang 712000,China;Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis,School of Pharmacy,School of Pharmacy,Shaanxi Institute of International Trade&Commerce,Xianyang 712046,China)

机构地区：[1]咸阳职业技术学院医药化工学院,陕西咸阳712000 [2]咸阳市分子影像与药物合成重点实验室,陕西国际商贸学院医药学院,陕西咸阳712046

出　　处：《化学研究与应用》2023年第11期2795-2800,共6页Chemical Research and Application

基　　金：陕西省自然科学基础研究计划(面上)项目(2022JM-561)资助;咸阳职业技术学院博士科研基金项目(2021BK01)资助;陕西国际商贸学院“中药药效物质研究”创新团队资助项目(SSY18TD02)资助。

摘　　要：本文报道一种川芎嗪衍生物3,5,6-三甲基-哌嗪-2-甲醛(1)的合成。以川芎嗪(2)为原料,依次经过单氮氧化、酰化重排、酯水解及氧化等4步反应得到目标化合物(1)。产物及中间体结构经核磁共振氢谱、碳谱、元素分析及质谱表征。醇氧化反应工艺研究发现,3,5,6-三甲基-哌嗪-2-甲醛(1)的适宜合成条件为:2-碘酰基苯甲酸(IBX)用量为n(IBX):n(3,5,6-三甲基吡嗪-2-甲醇)=1.5:1;反应溶剂为二甲基亚砜;25℃反应1.5 h,在该工艺条件下,产物收率达到91.5%[以3,5,6-三甲基吡嗪-2-甲醇(化合物5)计]。The synthesis of a ligustrazine derivative 3,5,6-trimethyl-piperazin-2-carbaldehyde(1)was reported.The target compound(1)was obtained through single-nitrogen oxidation,acylation rearrangement,ester hydrolysis and oxidation by using ligustrazine(2)as raw material.The structures of the product and intermediates were characterized by^(1)H NMR,^(13)C NMR,elemental analysis and mass spectrometry.The reaction conditions were investigated,and the suitable conditions for the alcohol oxidation reaction were de-termined as follows:the dosage of 2-iodoylbenzoic acid(IBX)was n(IBX):n((3,5,6-trimethylpyrazin-2-yl)methanol)=1.5:1;the reaction solvent is dimethyl sulfoxide;the yield of the product was up to 91.5%under the conditions of reaction at 25℃for1.5 h[calculated by(3,5,6-trimethylpyrazin-2-yl)methanol(compound 5)].

关 键 词：川芎嗪衍生物 氮氧化反应 酰化重排反应 醇氧化反应 

分 类 号：O626.4[理学—有机化学]