3-(2-甲氧基吡啶-3-基)喹啉-4(1H)-酮的合成研究  

Study on the synthesis of 3-(2-methoxypyridin-3-yl)quinolin-4(1 H )-ones

作　　者：张颖 胡玟奇 代凯莉 于丽芳 刘婷 汤杰 杨帆 ZHANG Ying;HU Min-qi;DAI Kai-li;YU Li-fang;LIU Ting;TANG Jie;YANG Fan(Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development,School of Chemistry and Molecular Engineering,East China Normal University,Shanghai 200062,China;Shanghai Greenchem&Biotech Co.,Ltd.,Shanghai 200062,China)

机构地区：[1]华东师范大学化学与分子工程学院上海分子治疗与新药创制工程技术研究中心,上海200062 [2]上海格苓凯生物科技有限公司,上海200062

出　　处：《化学试剂》2021年第11期1586-1594,共9页Chemical Reagents

基　　金：上海市科委项目(20142201500)。

摘　　要：发展了标题化合物的新合成方法。以2′-硝基吡啶查尔酮环氧化物为底物,经重排反应和分子内还原-环化反应合成目标化合物。通过考察催化剂、还原剂、反应温度对反应的影响,获得最优反应条件。该方法具有良好的官能团兼容性,通过此方法可以高效快速构建系列标题化合物,此外,该系列化合物亦可作为关键中间体经交叉偶联反应进行衍生化,构建结构更丰富的系列杂环化合物以应用于新药发现研究。所有产物均通过^1HNMR、^(13)CNMR和HR-MS等分析方法进行了结构表征。A convenient one-pot method for the synthesis of title compound has been developed.Rearrangment of 2′-nitropyridine chalcone epoxide followed by intramolecular reduction-cyclization reaction afforded the title compound with high yields.The optimal reaction conditions were found by exploring the influence of catalyst,reducing agent and temperature.The method has good functional group compatibility.A series of title compounds can be synthesized by this method,and can be derivatized to construct richer heterocyclic compounds as key intermediates through cross-coupling reactions,which can be used for new drug discovery research.All compounds were characterized by 1HNMR,13 CNMR and HRMS.

关 键 词：3-(2-甲氧基吡啶-3-基)喹啉-4(1H)-酮 2′-硝基吡啶查尔酮环氧化物 重排反应 分子内还原-环化反应 Suzuki交叉偶联反应 

分 类 号：O625.8[理学—有机化学]