低共熔溶剂/苯磺酸: 通过Biginelli反应合成二氢嘧啶酮类化合物的环境友好催化体系
收稿日期: 2022-06-02
修回日期: 2022-07-12
网络出版日期: 2022-08-10
基金资助
江西省教育厅自然科研基金(GJJ201611)
Deep Eutectic Solvent/Benzenesulfonic Acid: An Environmental Friendly Catalyst System towards the Synthesis of Dihydropyrimidinones via Biginelli Reaction
Received date: 2022-06-02
Revised date: 2022-07-12
Online published: 2022-08-10
Supported by
Science Foundation of Jiangxi Provincial Office of Education(GJJ201611)
在氯化胆碱和乙二醇组成的低共熔溶剂中, 苯磺酸催化下的Biginelli反应合成二氢嘧啶酮类化合物, 反应选择性高、产物易于分离、反应条件温和. 在较低温度下(50 ℃), 反应10.0 h, 得到94%的收率, 通过简单过滤产物即可分离, 且纯度较高. 该催化体系可以循环利用, 在此反应过程中催化剂、溶剂和没有反应的原料, 不需要进一步分离就可以进入下一次反应过程. 实验结果表明, 该催化体系循环利用8次后催化性能没有明显降低. 该反应体系对F、Cl、OMe、CH3和CH3CONH基团具有较好的容忍性, 共合成了20个产物, 收率79%~99%.
关键词： 低共融溶剂; Biginelli反应; 二氢嘧啶酮; 对甲苯磺酸
郑露露 , 王雨晴 , 李小港 , 张文彬 . 低共熔溶剂/苯磺酸: 通过Biginelli反应合成二氢嘧啶酮类化合物的环境友好催化体系[J]. 有机化学, 2022 , 42(11) : 3714 -3720 . DOI: 10.6023/cjoc202206002
In a deep eutectic solvent (DES) that composed of choline chloride and ethylene glycol, 3,4-dihydropyrimidin- 2(1H)-ones were synthesized via Biginelli reaction catalyzed by p-toluenesulfonic acid (p-TSA). 3,4-Dihydropyrimidin-2(1H)- ones were synthesized under mild conditions with high yield. High purity products were obtained by direct filtration without further purification. This catalytic system can be recycled, and the catalysts, solvents and remaining reactants can be directly recycled without separation. The results showed that the catalyst can be recycled up to 8 times. A wide variety of groups such as F, Cl, OMe, NO2, CH3, and CH3CONH were tolerated in this procedure, and 20 products were obtained in high yields (79%~99%).
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