有机化学 ›› 2014, Vol. 34 ›› Issue (12): 2462-2470.DOI: 10.6023/cjoc201410017 上一篇    下一篇

研究论文

吡咯烷酮衍生物的直接胺化: 构建偕二胺衍生物

杨锦明a, 褚雪强b, 纪顺俊b   

  1. a. 江苏省滩涂生物资源与环境保护重点建设实验室 盐城师范学院化学化工学院 盐城 224002;
    b. 江苏省有机合成重点实验室 苏州大学材料与化学化工学部 苏州 215123
  • 收稿日期:2014-10-11 修回日期:2014-10-22 发布日期:2014-10-23
  • 通讯作者: 纪顺俊 E-mail:shunjun@suda.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21172162,21372174)和江苏省优势学科资助项目.

Direct Amination of N-Acyliminium Ion Surrogates: A Convenient Access to gem-Diamines Derivatives

Yang Jinminga, Chu Xueqiangb, Ji Shunjunb   

  1. a. Key Laboratory of Coastal Wetland Bioresources and Environmental Protection of Jiangsu Province, College of Chemistry and Chemical Engineering, Yancheng Teachers University, Yancheng 224002;
    b. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123
  • Received:2014-10-11 Revised:2014-10-22 Published:2014-10-23
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21172162, 21372174) and the Project Funded by the Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions.

研究了对甲苯磺酸(PTSA)催化的吡咯烷酮化合物与各种N-亲核试剂的胺化反应. 该方法通过简单抽滤就能以中等至优良产率得到一系列的偕二胺化合物, 后处理简单无需柱层析, 且可以将反应放大至克级规模.

关键词: 酰亚胺离子, 偕二胺, 绿色化学

A novel 4-methylbenzenesulfonic acid (PTSA)-catalyzed intermolecular amination of N-acyliminium species with various N-sources via benzylic C(sp3)-O activation of functionalized 2-oxo-1-pyrrolidine derivatives has been developed. This method provides an efficient and chromatography-free access to gem-diamines equivalent with moderate to good yields. Because of the importance of gem-diamine derivatives, the methodology is expected to have a significant value for practical applications.

Key words: N-acyliminium ion, gem-diamines, green chemistry