CeCl3·7H2O-NaI-SiO2催化氨基苯硫酚与高位阻α,β-不饱和酮的迈克尔加成-缩合串联反应的研究.pdf

第27卷第9期
化学研究与应用
Vol27. No 9
2015年9月
Chemical Research and Application
Sep.,2015
文章编号:1004-1656(2015)09-1264-13
CeCl2'7H20-NalL-SiO2催化氨基苯硫酚与高位阻
a,8-不饱和酮的迈克尔加成-缩合串联反应的研究
高丽叶2,吕芳,李媛,李文红
(1.河北工业职业技术学院环境与化学工程系河北石家庄050091;
2.河北师范大学化学与材料科学学院,河北石家庄050024)
摘要:研究了复合型催化剂CeCl37H2O-NaI-SiO2催化氨基苯硫酚与高位阻,B-不饱和酮(1a-1u)的迈克尔
加成缩合串联反应。结果表明,该催化剂能有效地催化高位阻a,B-不饱和嗣与2-氨基苯硫酚和2-氨基4-氯
苯硫酚的迈克尔加成缩合串联反应。其最优条件是:n(CeCl37H20):n(NaI):n(SiO2):a(a,B-不饱和酮)=
1:2:10:2;溶剂为CHCl3,加热回流反应4h,反应收率较高(60%左右)。催化剂重复使用4次催化效果稳定。
关缝词:CeCl3'7H2O-NaI-SiO2;催化;a,B-不饱和酮;近克尔加成缩合串联反应
中图分类号:0626文献标志码:A
Michael addition-condensation tandem reactions of aminothiophenol with
a, B-unsaturated ketones with high steric hindrance
catalyzed by Ceci; 7H, O-NAI-SI0
GAO Li-ye", LV Fang, LI Yuan, LI Wen-hong
(1. Department of Environment and Chemical Engineering, Hebei College of Industry and Technology, Shijiazhuang05009, China
2. College of Chemistry Material Science, Hebei Normal University, Shijiazhuang050024, China)
Abstract: In this paper, the Michael addition-condensation tandem reactions of
o-aminothiophnen
unsatura
(1a-1n )catalyzed by CECI; 7HO-NAI-SIO were systematically studied. The results showed that the Cecl,.7h0-nai-sio,system
worked well for the reaction of the 2-amino hiopenol and 4clor--aminthiophenol with the a, B-unsaturated ketones. Uinder the
optimal reaction condit ons n(ec 7 H (Nal): n (i -unsa uae ketones)=I 2: 10: 2, the reaction time of4
h. at reflux te
erature and CHCL, as solvent, the reactions proceed with more higher yields( about 60%). The catalyst was basical
ly stable after recycling the conjugate addition reaction four times
Key words: Ce Cl 7 H0-NAL-SI02; ca al ysis B-unsaturated ke ones; Michael addition-condensation tandem reaction
迈克尔加成反应是有机合成反应中一类重要碳-硫键、碳-氮键等,这类反应不仅可以实现碳
而应用普遍的反应,它通过底物与不同的亲核试
剂发生反应,可以很方便的构筑碳-碳键、碳-氧键
链的延长,而且能够有效地引入杂原子,从而形成
收稿日期:2014-12-24;修回日期:201505-2
基金项目:国家自然科学基金项目(20972040)资助;河北省教育厅青年基金项目(Q2012001)资助
联系人简介:李文红(1977-),女,副教授,主要从事有机合成。E-mail:wenhong2006@126.com