以缺电子炔烃为原料经1,3-偶极环加成反应合成3-芳基中氮茚的新方法有机化学.pdfVIP

DOI: 10.6023/cjoc201401001 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 以缺电子炔烃为原料经1,3-偶极环加成反应合成 3-芳基中氮茚的新方法 李国栋a,b 胡华友*,a,b 阚玉和*,a,b 马奎蓉b (a 东北师范大学化学学院 长春 130024) (b 淮阴师范学院化学化工学院 淮安 223300) 摘要 报道了一种简便有效地合成 3-芳基中氮茚的方法. 反应需要的吡啶鎓盐可以用吡啶和苄卤很容易制得, 然后以 1,4-二氧六环为溶剂, 在碳酸铯存在的条件下与缺电子炔烃经 1,3-偶极环加成和芳构化反应即可得到 3-芳基中氮茚, 产 率 34%～81%. 该方法具有原料易得、操作简便、反应条件温和、选择性好等优点. 关键词 中氮茚; 1,3-偶极环加成; 缺电子炔烃 New Method for Synthesis of 3-Arylindolizines from Electron- Deficient Alkynes through 1,3-Dipolar Cycloaddition Li, Guodonga,b Hu, Huayou*,a,b Kan, Yuhe*,a,b Ma, Kuirongb a ( Department of Chemistry, Northeast Normal University, Changchun 130024) b ( School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300) Abstract A novel and efficient procedure for the preparation of 3-aryl-indolizine by 1,3-dipolar cycloaddition was estab- lished. The pyridinium salts were prepared from the corresponding pyridines and benzyl halides. In the presence of cesium carbonate, electron-deficient alkynes reacted with the pyridinium salts in 1,4-dioxane through 1,3-dipolar cycloaddition fol- lowed by an aromatization reaction to generate the corresponding 3-aryl-indolizines. This method features cheap reagents, a simple workup procedure, mild conditions, high regioselectivity and generating the desired products in moderate to high yield (34%～81%). Keywords indolizine; 1,3-dipo