[1]余 飞,黄荣璐,徐 绘,等.邻氨基二苯乙烯与1,3-环己二酮的串联环化反应合成1,4-二氢喹啉衍生物[J].常州大学学报(自然科学版),2019,31(03):34-39.[doi:10.3969/j.issn.2095-0411.2019.03.003]
 YU Fei,HUANG Ronglu,XU Hui,et al.Synthesis of 1,4-Dihydroquinoline Derivatives via Cascade Cyclization of o-Aminodistyrene with 1,3-Cyclohexanedione[J].Journal of Changzhou University(Natural Science Edition),2019,31(03):34-39.[doi:10.3969/j.issn.2095-0411.2019.03.003]
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邻氨基二苯乙烯与1,3-环己二酮的串联环化反应合成1,4-二氢喹啉衍生物()
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常州大学学报(自然科学版)[ISSN:2095-0411/CN:32-1822/N]

卷:
第31卷
期数:
2019年03期
页码:
34-39
栏目:
化学化工
出版日期:
2019-05-28

文章信息/Info

Title:
Synthesis of 1,4-Dihydroquinoline Derivatives via Cascade Cyclization of o-Aminodistyrene with 1,3-Cyclohexanedione
文章编号:
2095-0411(2019)03-0034-06
作者:
余 飞黄荣璐徐 绘张 泽
(安徽工程大学 生物与化学工程学院,安徽 芜湖 241000)
Author(s):
YU Fei HUANG Ronglu XU Hui ZHANG Ze
(School of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, China)
关键词:
14-二氢喹啉 迈克尔加成 串联反应
Keywords:
14-dihydroquinoline iodine Michael addition cascade reaction
分类号:
O 621.3
DOI:
10.3969/j.issn.2095-0411.2019.03.003
摘要:
先以廉价易得的取代苯胺和苯乙炔为底物合成邻氨基二苯乙烯,再与1,3-环己二酮在甲苯中碘催化作用下加热反应,通过缩合-加成串联环化反应高效合成了8个新型的1,4-二氢喹啉类衍生物,分离产率高达85%~94%,并通过熔点、核磁1H NMR及13C NMR分析手段对所有产物进行了结构表征。该方法原料及催化剂便宜易得,操作简便,合成效率高。
Abstract:
Firstly, o-aminodistyrenes were synthesized from cheap and easily available substituted anilines and phenylacetylenes. The condensation-addition cascade cyclization of these o-aminodistyrenes with 1,3-cyclohexadiones can be efficiently accomplished by heating in toluene in presence of iodine. Following this method, eight novel 1,4-dihydroquinolines were obtained in 85%—94% isolated yields. All the products were characterized by melting point, 1H NMR and 13C NMR analysis. This method exhibits advantages of using cheap and easily available starting materials and catalyst, easy operation and high efficiency.

参考文献/References:

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备注/Memo

备注/Memo:
收稿日期:2018-10-20。
基金项目:国家自然科学基金资助项目(21242013); 国家级大学生创新训练计划(201810363053)。
作者简介:余飞(1993—),男,安徽安庆人,硕士生。通信联系人:张泽(1976—),E-mail: zzhang@ahpu.edu.cn
更新日期/Last Update: 2019-05-29