无过渡金属催化条件下咪唑衍生物与炔基溴的炔基化反应研究有机化学.pdfVIP

DOI: 10.6023/cjoc201401008 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 无过渡金属催化条件下咪唑衍生物与炔基溴的炔基化反应研究 于敬阳 彭进松 岳亦霞 赵宇卓 陈春霞* (东北林业大学理学院化学化工系 哈尔滨 150040) 摘要 以炔基溴和咪唑衍生物为反应原料, 详细探讨了无过渡金属催化条件下的咪唑类芳香炔胺化合物的合成方法. 研究结果表明, 以N,N-二甲基甲酰胺为溶剂、碳酸钾为碱, 于 80 ℃下反应 12 h 即可获得中等偏上收率的碳-氮偶联产 1 13 物. 通过上述方法合成得到了系列芳香炔胺衍生物, 其结构经 H NMR 和 C NMR 表征. 关键词 无过渡金属催化; 咪唑衍生物; 炔基溴; 碳-氮交叉偶联; 芳香炔胺 Transition-Metal-Free Alkynylation of Imidazoles with Alkynyl Bromides Yu, Jingyang Peng, Jinsong Yue, Yixia Zhao, Yuzhuo Chen, Chunxia* (Department of Chemistry and Chemical Engineering, College of Science, Northeast Forestry University, Harbin 150040) Abstract Transition-metal-free alkynylation of imidazoles with alkynyl bromides was examined in detail. With K CO as 2 3 base in N,N-dimethylformamide (DMF) at 80 ℃ for 12 h, the reaction afforded the corresponding carbon-nitrogen cross-coupling products in moderate yield. Imidazole-based aromatic ynamines were synthesized by the above method, and the structure was characterized by 1H NMR and 13C NMR spectra. Keywords transition-metal-free; imidazoles; alkynyl bromides; C—N cross-coupling; aromatic ynamines 炔胺是一类氮原子与炔基官能团直接相连的重要 NH2 R O 化合物, 许多芳香炔胺衍生物, 如 9 N