One Pot Tandem P-Michael Addition/SN2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives

doi:10.6023/cjoc202402002

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2241-2250.DOI: 10.6023/cjoc202402002 Previous Articles Next Articles

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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

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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Abstract

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

Cite this article

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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Fig. & Tab. 7

Figure 1. Bioactive molecules and drugs containing the quinoline scaffold

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

Table 1. Optimization of the reaction conditions

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

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

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

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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