Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1792-1796.DOI: 10.6023/cjoc201501005 Previous Articles     Next Articles



金海明a, 邹亮a, 陈南雨a, 孙圆圆a, 罗书平a, Junge Henrikb, Beller Matthiasb   

  1. a 浙江工业大学化学工程学院 绿色化学合成技术国家重点实验室培育基地 杭州 310014;
    b 罗斯托克大学莱布尼茨催化研究所 罗斯托克 18059 德国
  • 收稿日期:2015-01-05 修回日期:2015-03-20 发布日期:2015-04-10
  • 通讯作者: 罗书平
  • 基金资助:

    国家自然科学基金(Nos. 21361130021, 21376222)资助项目.

Design and Synthesis of Novel 1,10-Phenanthroline Derivatives

Jin Haiminga, Zou Lianga, Chen Nanyua, Sun Yuanyuana, Luo Shupinga, Henrik Jungeb, Matthias Bellerb   

  1. a State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
    b Leibniz Institute for Catalysis at the University of Rostock LIKAT, Rostock 18059, Germany
  • Received:2015-01-05 Revised:2015-03-20 Published:2015-04-10
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21361130021, 21376222).

To access functionalized nitrogen ligands, a series of novel 1,10-phenanthroline derivatives 1a~1d were designed and synthesized. Starting from 1-bromoaryl-3-chloroacetone (2) and o-phenylenediamine (3), 4,7-dibromoaryl-1,10-phenanthroline (4) were obtained in up to 64% yield by using a straightforward one-pot method catalyzed by mixed acids. Next, halogen lithium exchange reactions were performed to give 4. Finally, quenching of the reaction mixture with CO2 gave the desired 2,9-dialkyl-4,7-bis(carboxy-aryl)-1,10-phenanthroline derivatives 1 in up to 59% yield. This work provides a simple and convenient route to synthesize new 2,9-alkylated carboxylic acid-functionalized phenanthrolines.

Key words: 1,10-phenanthroline derivatives, o-phenylenediamine, one pot, carboxylic acid