可见光促进三组分合成C3-芳甲基取代的咪唑并[1,2-a]吡啶衍生物  

Synthesis of C3-Arylmethyl Substituted Imidazo[1,2-a]pyridines via Visible-light-promoted Three-component Reaction

作　　者：张玉凤 张杰 王天骏 黄雨聪 李玉秀 刘平[2] ZHANG Yufeng;ZHANG Jie;WANG Tianjun;HUANG Yucong;Li Yuxiu;LIU Ping(School of Animal Pharmaceutical,Jiangsu Agri-animal Husbandry Vocational College,Taizhou 225300,China;School of Chemistry and Materials Science,Nanjing Normal University,Nanjing 210023,China)

机构地区：[1]江苏农牧科技职业学院动物药学院,江苏泰州225300 [2]南京师范大学化学与材料科学学院,江苏南京210023

出　　处：《合成化学》2024年第1期59-66,共8页Chinese Journal of Synthetic Chemistry

基　　金：江苏省大学生创新计划项目(202112806014Y);江苏省高校自然科学基金面上项目(21KJB150008);江苏农牧科技职业学院2021年度和2022年度“凤凰学子”人才培养计划项目。

摘　　要：C3-芳甲基取代的咪唑并[1,2-a]吡啶衍生物在材料及药物化学领域有着广泛应用。基于自由基对亚胺C=N键的插入串联环化策略,以2-氨基吡啶衍生物、芳基甲醛为原料、芳基溴乙炔为自由基源,在可见光促进和路易斯酸协同作用下,通过三组分串联反应,以70%~78%的产率实现了C3-芳甲基取代的咪唑并[1,2-a]吡啶衍生物的构建。目标产物结构经^(1)H NMR、^(13)C NMR和HR-MS确证。本方法无需额外添加光催化剂,操作简便、反应条件温和,具有较好的底物适用性和官能团耐受性,并且可以应用于唑吡坦的一步合成。C3-arylmethylated imidazo[1,2-a]pyridines were widely used in the field of materials and pharmaceutical chemistry.In this study,using 2-aminopyridines,aryl formaldehydes and aryl bromoacetylenes as substrates,C3-arylmethylated imidazo[1,2-a]pyridines were successfully achieved through visible light-promoted three-component reaction with the synergistic effect of the lewis acid based the radical insertion to the C=N bond of imines/cyclization cascade strategy.The yields of the reaction were 70%~78%and the product structures were confirmed by^(1)H NMR,^(13)C NMR and HR-MS analyses.The method has advantages of no photocatalyst needing,the convenient operations,the mild reaction conditions,the wide substrate suitability and the good functional group tolerance,which provides the one stage synthetic approach for zolpidem.

关 键 词：可见光促进 路易斯酸 三组分反应 芳甲基化 串联环化 无外加光催化剂 咪唑并[1 2-a]吡啶 

分 类 号：O621.25[理学—有机化学]