氮杂邻亚甲基苯醌的P-迈克尔加成/SN2/分子内Wittig反应的一锅法串联反应构建2,3-二取代二氢喹啉衍生物

doi:10.6023/cjoc202402002

有机化学 ›› 2024, Vol. 44 ›› Issue (7): 2241-2250.DOI: 10.6023/cjoc202402002 上一篇下一篇

研究论文

氮杂邻亚甲基苯醌的P-迈克尔加成/S_N2/分子内Wittig反应的一锅法串联反应构建2,3-二取代二氢喹啉衍生物

刘雨迪, 程行, 何照林^*(), 陈伟^*()

武汉工程大学化学与环境工程学院新型反应器与绿色化学工艺湖北省重点实验室武汉 430205

收稿日期:2024-02-02 修回日期:2024-03-13 发布日期:2024-04-24
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(21702155)

One Pot Tandem P-Michael Addition/S_N2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives

Yudi Liu, Hang Cheng, Zhaolin He(), Wei Chen()

Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205

Received:2024-02-02 Revised:2024-03-13 Published:2024-04-24
Contact: * E-mail: zlhe3251@wit.edu.cn;wchen@wit.edu.cn
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21702155)

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摘要/Abstract

报道了原位生成的氮杂邻亚甲基苯醌中间体与三苯基膦、α-溴代酮发生P-迈克尔加成/S_N2/分子内Wittig反应的一锅法串联反应. 该反应以25%~93%的收率提供了一种高效、温和的构建2,3-二氢喹啉衍生物的方法. 此外, 还可以通过反应条件的简单改变, 得到的2,3-二取代的喹啉衍生物.

关键词: 氮杂邻亚甲基苯醌, 二氢喹啉衍生物, 喹啉衍生物

A one-pot tandem P-Michael addition/S_N2/intramolecular Wittig Reaction of in situ generated aza-o-quinone methides with PPh₃ and α-bromo ketones has been reported. This protocol provided an efficient and mild approach to synthesize 2,3-disubstituted dihydroquinolines in 25%~93% yields. In addition, the 2,3-disubstituted quinolines could also be obtained by simply modification of the reaction conditions.

Key words: aza-o-quinone methides, dihydroquinoline derivatives, quinoline derivatives

引用此文

刘雨迪, 程行, 何照林, 陈伟. 氮杂邻亚甲基苯醌的P-迈克尔加成/S_N2/分子内Wittig反应的一锅法串联反应构建2,3-二取代二氢喹啉衍生物[J]. 有机化学, 2024, 44(7): 2241-2250.

Yudi Liu, Hang Cheng, Zhaolin He, Wei Chen. One Pot Tandem P-Michael Addition/S_N2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2241-2250.

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图/表 7

图1. 含喹啉骨架的生物活性分子及药物分子

Figure 1. Bioactive molecules and drugs containing the quinoline scaffold

图式1. aza-o-QMs参与的串联反应构建苯并含氮杂环化合物

Scheme 1. Tandem reaction of aza-o-QMs to construction nitro- gen containing compounds

表1. 反应条件的优化a

Table 1. Optimization of the reaction conditions

表2. N-(2-(氯甲基)苯基)-4-甲基苯磺酰胺1的底物拓宽a

Table 2. Substrate scope for N-(2-(chloromethyl)-phenyl)-4- methylbenzenesulfonamides 1

表3. α-溴代芳香酮2的底物拓宽a

Table 3. Substrate scope for α-bromo aromatic ketones 2

表4. α-溴代烷基酮2的底物拓宽a

Table 4. Substrate scope for α-bromo alkyl ketones 2

图式2. 克级规模的反应及反应产物的转化

Scheme 2. Gram-scale experiment and synthetic transformations

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氮杂邻亚甲基苯醌的P-迈克尔加成/S_N2/分子内Wittig反应的一锅法串联反应构建2,3-二取代二氢喹啉衍生物

One Pot Tandem P-Michael Addition/S_N2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives

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