以2-氨基苯甲醛合成四氢呋喃并[3,2-b]喹啉-2(3H)-酮类化合物的Aldol/Michael加成串联反应

doi:10.5246/jcps.2017.03.016

中国药学(英文版) ›› 2017, Vol. 26 ›› Issue (3): 163-172.DOI: 10.5246/jcps.2017.03.016

• 【研究论文】 • 下一篇

以2-氨基苯甲醛合成四氢呋喃并[3,2-b]喹啉-2(3H)-酮类化合物的Aldol/Michael加成串联反应

季泠, 尹大伟, 王欣^*, 李润涛^*

北京大学医学部药学院天然药物及仿生国家重点实验室, 北京 100191

收稿日期:2016-11-29 修回日期:2017-02-05 出版日期:2017-03-30 发布日期:2017-02-23
通讯作者: Tel.: +86-010-82801504, Fax: +86-010-82716956, E-mail: xinwang@bjmu.edu.cn, lirt@bjmu.edu.cn
基金资助:
National Natural Science Foundation of China (Grant No. 21372019).

Synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-one derivatives from 2-aminobenzaldehydes and α-angelica lactone via a tandem Aldol/Michael addition

Ling Ji, Dawei Yin, Xin Wang^*, Runtao Li^*

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University Health Science Center, Beijing 100191, China

Received:2016-11-29 Revised:2017-02-05 Online:2017-03-30 Published:2017-02-23
Contact: Tel.: +86-010-82801504, Fax: +86-010-82716956, E-mail: xinwang@bjmu.edu.cn, lirt@bjmu.edu.cn
Supported by:
National Natural Science Foundation of China (Grant No. 21372019).

摘要/Abstract

摘要： 本文发展了一种由当归内酯和邻氨基苯甲醛衍生物出发, 经Aldol/Michael串联合环反应构建四氢呋喃并[3,2-b]喹啉-2(3H)-酮类化合物的新方法。底物于DBU催化下, 在异丙醇中0 ºC反应, 即可以较高收率得到四氢呋喃并喹啉酮类衍生物, 具有条件温和, 原子经济性高, 反应速率快等优点。

关键词: Adol/Michael 串联合环反应, 四氢喹啉, 呋喃酮

Abstract:

An efficient synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-ones from α-angelica lactone and 2-aminobenzaldehydes via a tandem Aldol-Michael addition is described. The reactions were carried out using DBU as the base in i-PrOH at 0 °C, affording tetrahydrofuro[3,2-b]quinolin-2(3H)-ones in moderate to good yields.

Key words: Aldol/Michael tandem cyclization, Tetrahydroquinoline, Furanone

中图分类号:

R916

Supporting:

季泠, 尹大伟, 王欣, 李润涛. 以2-氨基苯甲醛合成四氢呋喃并[3,2-b]喹啉-2(3H)-酮类化合物的Aldol/Michael加成串联反应[J]. 中国药学(英文版), 2017, 26(3): 163-172.

Ling Ji, Dawei Yin, Xin Wang, Runtao Li. Synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-one derivatives from 2-aminobenzaldehydes and α-angelica lactone via a tandem Aldol/Michael addition[J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(3): 163-172.

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以2-氨基苯甲醛合成四氢呋喃并[3,2-b]喹啉-2(3H)-酮类化合物的Aldol/Michael加成串联反应

Synthesis of tetrahydrofuro[3,2-b]quinolin-2(3H)-one derivatives from 2-aminobenzaldehydes and α-angelica lactone via a tandem Aldol/Michael addition

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