Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 800-810.DOI: 10.6023/cjoc201808003 Previous Articles     Next Articles



唐子龙a,b, 汪明a,b, 姚园a,b, 谭经照a,b, 代宁宁a,b, 李新兴a,b, 彭丽芬a, 焦银春b   

  1. a 湖南科技大学理论有机化学与功能分子教育部重点实验室 湘潭 411201;
    b 湖南科技大学化学化工学院 精细聚合物可控制备及功能应用湖南省重点实验室 湘潭 411201
  • 收稿日期:2018-08-06 修回日期:2018-09-10 发布日期:2018-10-26
  • 通讯作者: 唐子龙
  • 基金资助:


Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes

Tang Zilonga,b, Wang Minga,b, Yao Yuana,b, Tan Jingzhaoa,b, Dai Ningninga,b, Li Xinxinga,b, Peng Lifena, Jiao Yinchunb   

  1. a Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201;
    b Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201
  • Received:2018-08-06 Revised:2018-09-10 Published:2018-10-26
  • Contact: 10.6023/cjoc201808003
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21877034, 21372070) and the Scientific Research Fund of Hunan Provincial Education Department (No. 17A066).

Lewis acid La(OTf) 3-catalyzed chemoselective cyclization of hydroxyl substituted ethylenediamine derivatives with aldehydes has been described for the first time, which provides efficient access to diversely functionalized 1,3-imidazoli-dines and 3,1-benzoxazines in generally good yields only by adjusting the position of the methylene group within hydroxyl substituted ethylenediamines. The reaction is suitable to aromatic aldehydes and aliphatic ones. Plausible mechanisms are also proposed to explain the observed reaction modes, wherein the nucleophilicity of nitrogen and oxygen atoms plays an important role in controlling the chemoselectivity.

Key words: hydroxyl substituted ethylenediamine, 1,3-imidazolidine, 3,1-benzoxazine, chemoselectivity, synthesis