Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1875-1880.DOI: 10.6023/cjoc201405008 Previous Articles     Next Articles

三步缩合法合成2-苯基-1-羟基联三苯叉

王文丽a, 何清a,b, 丁茹a, 贺云a, 张尊听a   

  1. a 陕西师范大学化学化工学院, 教育部药用资源与天然药物化学重点实验室, 西北濒危药材资源开发国家工程实验室, 西安 710062;
    b 温州大学化学与材料工程学院, 温州 325027
  • 收稿日期:2014-03-06 修回日期:2014-03-27 出版日期:2014-09-25 发布日期:2014-06-03
  • 通讯作者: 张尊听 E-mail:zhangzt@snnu.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21372150)、陕西省自然科学基础研究计划(No. 2014JQ2073)和中央高校基本科研业务费专项资金(No. GK261001095)资助项 目.

Synthesis of 1-Hydroxy-2-phenyltriphenylene Derivatives by Three-Step Condensation

Wang Wenlia, He Qinga,b, Ding Rua, He Yuna, Zhang Zuntinga   

  1. a Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062;
    b College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027
  • Received:2014-03-06 Revised:2014-03-27 Online:2014-09-25 Published:2014-06-03
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372150), the Natural Science Foundation of Shaanxi Province (No. 2014JQ2073) and the Fundamental Research Funds for the Central Universities (No. GK261001095).

(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-ones (2) were synthesized by the condensation reaction of o-hydroxyacetophenones (1) and N,N-dimethylformamide-dimethyl acetal (DMF-DMA). Using DMF as solvent and K2CO3 as base, 4'-phenyl-(1,1':2',1''-terphenyl)-2,3'-diol (3) were synthesized via the condensation reaction of intermediate 2 and 1,3-diphenylacetones. 3 were dissolved in the solution of acetonitrile-1% HCl (V:V=1:1) and irradiated by 500 W mercury lamp, and 1-hydroxy-2-phenyltriphenylenes were obtained. This process to synthesize 4 has the advantages of simple operation, high efficiency of the atomic, without oxidant and catalyst. Compounds 3 and 4 were confirmed by the method of FT-IR, 1H NMR, 13C NMR, HRMS.

Key words: 4'-phenyl-(1,1':2',1''-terphenyl)-2,3'-diol, 1-hydroxy-2-phenyltriphenylene, photocyclization reaction, condensation reaction