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
张玉凤 1张杰 1王天骏 1黄雨聪 1李玉秀 1刘平2
作者信息
- 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
- 折叠
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1H NMR、13C 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.
Abstract
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 bro-moacetylenes 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 1H NMR,13C 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Key words
visible light promotion/lewis acid/three-component reaction/arylmethylation/cyclization cascade strategy/photocatalyst-free/imidazo[1,2-a]pyridines引用本文复制引用
基金项目
江苏省大学生创新项目(202112806014Y)
江苏省高等学校自然科学研究面上项目(21KJB150008)
江苏农牧科技职业学院"凤凰学子"人才培养计划(2021-2022)()
出版年
2024
NETL
NSTL
维普
万方数据