三步缩合法合成2-苯基-1-羟基联三苯叉
收稿日期: 2014-03-06
修回日期: 2014-03-27
网络出版日期: 2014-06-03
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
Received date: 2014-03-06
Revised date: 2014-03-27
Online 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).
以邻羟基苯乙酮为原料,与N,N-二甲基甲酰胺-二甲基缩醛(DMF-DMA)分子间缩合合成(E)-3-二甲氨基-1-(2'-羟基苯基)-1-丙烯酮中间体(2); 中间体2与1,3-二苯基丙酮在以DMF为溶剂,K2CO3存在下发生缩合反应生成4'-苯基-2,3'-羟基-1,1':2',1''-三联苯类化合物(3); 化合物3以乙腈-1% HCl (V:V=1:1)为溶剂,汞灯500 W照射分子内脱水关环合成2-苯基-1-羟基联三苯叉类化合物(4). 三步缩合法合成2-苯基-1-羟基联三苯叉具有操作简单、无需氧化剂与催化剂、原子利用率高等优点. 采用FT-IR,1H NMR,13C NMR和HRMS对化合物3和4进行了表征.
王文丽 , 何清 , 丁茹 , 贺云 , 张尊听 . 三步缩合法合成2-苯基-1-羟基联三苯叉[J]. 有机化学, 2014 , 34(9) : 1875 -1880 . DOI: 10.6023/cjoc201405008
(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.
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