有机化学 ›› 2016, Vol. 36 ›› Issue (6): 1335-1340.DOI: 10.6023/cjoc201512050 上一篇    下一篇

研究论文

仲胺介入的丙炔酸甲酯与亚胺的环合反应

马鸿飞a, 黄浩a, 宿江岭b, 钮长盛a, 吴正光c, 卜洪忠a, 李玉峰a   

  1. a 南京工业大学化学与分子工程学院南京 211816;
    b 山东万博化工有限公司淄博 255000;
    c 南京大学化学化工学院南京 210093
  • 收稿日期:2015-12-31 修回日期:2016-01-20 发布日期:2016-02-24
  • 通讯作者: 李玉峰 E-mail:yufengli@njtech.edu.cn

Secondary Amine-Mediated Cyclization of Methyl Propiolate with Imines

Ma Hongfeia, Huang Haoa, Su Jianglingb, Niu Changshenga, Wu Zhengguangc, Bu Hongzhonga, Li Yufenga   

  1. aCollege of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816;
    b Shandong Wanbo Chemical Industry Corporation, Zibo 255000;
    c Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
  • Received:2015-12-31 Revised:2016-01-20 Published:2016-02-24

建立了一种合成四氢嘧啶衍生物的方法. 仲胺与丙炔酸甲酯发生Michael加成反应, 生成β-胺基丙烯酸酯; 向β-胺基丙烯酸甲酯及亚胺的混合物中加入有机酸, 常温下数分钟内发生环合反应得到四氢嘧啶衍生物, 仲胺以铵盐形式离去. 该反应对甲醛亚胺具有良好的适应性.

关键词: 丙炔酸甲酯, 亚胺, 胺介入反应, 四氢嘧啶衍生物

A facile method for the synthesis of tetrahydropyrimidines is described. Diethylamine was treated with methyl propiolate to provide Michael adduct (β-amino acrylate). In the presence of organic acid, the cyclization of imines with β-aminoacrylateoccurred at room temperature and completed within several minutes to give tetrahydropyrimidines with liberation of ammonium salt. Formaldimines show good toleration to the reaction.

Key words: methylpropiolate, imine, amine-mediated reaction, tetrahydropyrimidines