Synthesis of 2⁃Ethyl⁃2⁃Aryl⁃Dihydroquinoline Derivatives

doi:10.3969/j.issn.1672-6952.2022.05.003

Journal of Liaoning Petrochemical University ›› 2022, Vol. 42 ›› Issue (5): 18-25.DOI: 10.3969/j.issn.1672-6952.2022.05.003

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Synthesis of 2⁃Ethyl⁃2⁃Aryl⁃Dihydroquinoline Derivatives

Chaofan Zhu¹(), Rui Wang¹(), Yunrong Chen²

^1.School of Petrochemical Engineering，Liaoning Petrochemical University，Fushun Liaoning 113001，China
^2.School of Physical Science and Technology，ShanghaiTech University，Shanghai 201210，China

Received:2021-04-09 Revised:2021-04-23 Published:2022-10-25 Online:2022-11-18
Contact: Rui Wang

2⁃乙基⁃2⁃芳基⁃二氢喹啉衍生物的合成

朱超凡¹(), 王锐¹(), 陈运荣²

^1.辽宁石油化工大学石油化工学院，辽宁抚顺 113001
^2.上海科技大学物质科学与技术学院，上海 201210

通讯作者: 王锐
作者简介:朱超凡（1994⁃），男，硕士研究生，从事有机合成方面的研究；E⁃mail：18838978281@163.com。
基金资助:
国家自然科学基金项目(21901162)

Abstract

Abstract:

The synthesis method of 2?ethyl?2?aryl?dihydroquinoline derivatives was studied. The synthesis is divided into three steps: the first step, the Suzuki cross?coupling of 2?bromoquinoline and phenylboronic acid; the second step, the exchange of halide lithium; the third step, the nucleophilic addition of the organolithium reagent to the α?position of 2?phenylquinoline to obtain a double?substituted dihydroquinoline derivative. The drug with dihydroquinoline structure was synthesized by this method, and the target product was analyzed by various characterization methods, and the structure of the target product was confirmed.

Key words: Dihydroquinoline, Suzuki cross coupling, Lithium halide exchange, Nucleophilic addition

摘要：

研究了2?乙基?2?芳基?二氢喹啉衍生物的合成方法。合成分成三步：第一步，2?溴喹啉与苯硼酸进行Suzuki交叉偶联；第二步，进行卤锂交换；第三步，有机锂试剂在2?苯基喹啉的α位进行亲核加成，得到双取代二氢喹啉衍生物。通过此方法合成了具有二氢喹啉结构的药物，并通过各种表征手段对目标产物进行了分析，确认了目标产物的结构。

关键词: 二氢喹啉, Suzuki交叉偶联, 卤锂交换, 亲核加成

CLC Number:

TE624

Chaofan Zhu, Rui Wang, Yunrong Chen. Synthesis of 2⁃Ethyl⁃2⁃Aryl⁃Dihydroquinoline Derivatives[J]. Journal of Liaoning Petrochemical University, 2022, 42(5): 18-25.

朱超凡, 王锐, 陈运荣. 2⁃乙基⁃2⁃芳基⁃二氢喹啉衍生物的合成[J]. 辽宁石油化工大学学报, 2022, 42(5): 18-25.

Figures/Tables 15

References 14

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序号	溶剂	产率/%
1	甲苯	10
2	二氯甲烷	0
3	乙酸乙酯	0
4	乙醚	40
5	四氢呋喃	70

序号	溶剂	产率/%
1	甲苯	10
2	二氯甲烷	0
3	乙酸乙酯	0
4	乙醚	40
5	四氢呋喃	70

序号	反应温度/℃	溶剂	产率/%
1	－78	四氢呋喃	48
2	－40	四氢呋喃	55
3	－20	四氢呋喃	65
4	0	四氢呋喃	70

序号	反应温度/℃	溶剂	产率/%
1	－78	四氢呋喃	48
2	－40	四氢呋喃	55
3	－20	四氢呋喃	65
4	0	四氢呋喃	70

序号	溶剂	乙基锂体积/mL	产率/%
1	四氢呋喃	2.0	20
2	四氢呋喃	3.0	36
3	四氢呋喃	4.0	57
4	四氢呋喃	5.0	62
5	四氢呋喃	6.0	70

Synthesis of 2⁃Ethyl⁃2⁃Aryl⁃Dihydroquinoline Derivatives

2⁃乙基⁃2⁃芳基⁃二氢喹啉衍生物的合成

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Figures/Tables 15

References 14

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