Chem. J. Chinese Universities ›› 2019, Vol. 40 ›› Issue (4): 712.doi: 10.7503/cjcu20180663

• Organic Chemistry • Previous Articles     Next Articles

Synthesis of 6-Aminoformyl-substituted Phenanthridines Promoted by TBAC/TBHP System

DAI Jianan, YANG Ziqi, WEI Zhonglin, CAO Jungang, LIANG Dapeng, DUAN Haifeng*(), LIN Yingjie*()   

  1. College of Chemistry, Jilin University, Changchun 130012, China
  • Received:2018-09-29 Online:2019-12-24 Published:2018-12-24
  • Contact: DUAN Haifeng,LIN Yingjie E-mail:duanhf@jlu.edu.cn;linyj@jlu.edu.cn
  • Supported by:
    † Supported by the National Natural Science Foundation of China(No.51373067).

Abstract:

In the presence of simple K2HPO4, under catalytic oxidation of tetrabutylammonium chloride(TBAC) and tert-butyl hydroperoxide(TBHP), the couple reaction of 2-isocyanobiphenyl derivatives with N,N-dimethylformamide(DMF) was realized, and 6-aminoformyl-substituted phenanthridine compounds were obtained by formation of two C—C bonds in one pot reaction. A series of 2-isocyanobiphenyl derivatives containg electron-donating and withdrawing substituents was investigated. Corresponding 6-aminoformyl substituted phenanthridines were constructed in moderate to high yields(up to 86% yield), which would provide promising candidates for chemical biology and drug discover.

Key words: Cascade cyclization, Phenanthridine-6-carboxamide, 2-Isocyanobiphenyl derivative

CLC Number: 

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