Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2424-2437.DOI: 10.6023/cjoc201406007 Previous Articles     Next Articles



杨俊娟a, 史大昕a, 刘明星a, 张立军b, 张奇a, 李加荣a   

  1. a. 北京理工大学化工与环境学院 北京 100081;
    b. 天津理工大学化学化工学院 天津 300191
  • 收稿日期:2014-06-06 修回日期:2014-07-16 发布日期:2014-08-26
  • 通讯作者: 李加荣
  • 基金资助:


Structure of the Condensed Product of Aromatic o-Aminonitrile with Carbonyl Compound and Its Mechanism

Yang Junjuana, Shi Daxina, Liu Mingxinga, Zhang Lijunb, Zhang Qia, Li Jiaronga   

  1. a. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081;
    b. School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300191
  • Received:2014-06-06 Revised:2014-07-16 Published:2014-08-26
  • Supported by:

    Project supported by the Basic Research Fund of Beijing Institute of Technology (No. 2012CX100035).

Friedländer reaction is one of the most important routes to synthesize the quinoline and its derivatives, which possesses excellent bioactivity and photo-electricity activity. Recently, a new skeleton product besides the normal Friedländer quinoline was discovered by the condensation of aromatic o-aminonitrile and carbonyl compounds, and this phenomenon has attracted many researchers, but the skeleton structure of new conversion is debated. Herein, this paper reviews on the development progress of this new kind reaction. According to recent research results, the skeleton structure of new conversion was assigned as quinazolinone, which was confirmed by the 13C NMR, FT-IR, and single-crystal X-ray diffraction deterimations. Therefore, this new conversion is abbreviated as PDF conversion, which means a new conversion from Pinner to Dimroth rearrangement in the Friedländer reaction. The total reaction mechanism of o-aminonitrile with carbonyl compound was proposed.

Key words: aromatic o-aminonitrile, divergent conversion, Friedländer conversion, quinazolinone, benzoxazine, product structure