铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

doi:10.6023/cjoc202007003

有机化学 ›› 2021, Vol. 41 ›› Issue (1): 318-324.DOI: 10.6023/cjoc202007003 上一篇下一篇

研究论文

铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

秦锋^a, 汤琳^a, 黄飞^a, 李晓悦^a, 张武^a^,^*()

a 安徽师范大学化学与材料科学学院安徽芜湖 241000

收稿日期:2020-07-01 修回日期:2020-08-07 发布日期:2020-08-31
通讯作者: 张武
作者简介:
* Corresponding author. E-mail: zhangwu@ahnu.edu.cn
基金资助:
国家自然科学基金(21272006)

Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction

Feng Qin^a, Lin Tang^a, Fei Huang^a, Xiaoyue Li^a, Wu Zhang^a^,^*()

a College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

Received:2020-07-01 Revised:2020-08-07 Published:2020-08-31
Contact: Wu Zhang
Supported by:
the National Natural Science Foundation of China(21272006)

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摘要/Abstract

以苯胺、苯乙烯为原料, 二甲基亚砜(DMSO)为C1合成子, 开发了一种铜催化三组分反应合成喹啉衍生物的方法. 机理研究表明, 反应先形成亚胺中间体, 再发生Aza-Diels-Alder反应. 该方法具有高效、环境友好和底物适用范围广等特点.

关键词: 铜催化, 多组分反应, 喹啉衍生物, Aza-Diels-Alder反应

A tandem three-component reaction for the synthesis of quinolines from anilines, styrene and dimethyl sulfoxide (DMSO) has been developed. Dimethyl sulfoxide (DMSO) served as one-carbon synthon and solvent. The mechanism studies revealed that imine intermediate was involved and inverse electron demand Aza-Diels-Alder reaction was occurred. This method is featured by environmentally benign, good functional group tolerance and good to excellent yield.

Key words: copper-catalyzed, multi-component reaction, quinoline derivatives, Aza-Diels-Alder reaction

引用此文

秦锋, 汤琳, 黄飞, 李晓悦, 张武. 铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉[J]. 有机化学, 2021, 41(1): 318-324.

Feng Qin, Lin Tang, Fei Huang, Xiaoyue Li, Wu Zhang. Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 318-324.

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Entry	Catalyst	Oxidant	Solvent	Yield ^b /%
1	CuBr	K ₂S ₂O ₈	DMF	37
2	CuBr	K ₂S ₂O ₈	DMA	23
3	CuBr	K ₂S ₂O ₈	DMSO	67
4	CuBr	K ₂S ₂O ₈	NMP	nr
5	Cu(OAc) ₂	K ₂S ₂O ₈	DMSO	34
6	CuCl ₂	K ₂S ₂O ₈	DMSO	38
7	CuBr ₂	K ₂S ₂O ₈	DMSO	41
8	CuCl	K ₂S ₂O ₈	DMSO	58
9	CuI	K ₂S ₂O ₈	DMSO	76
10	—	K ₂S ₂O ₈	DMSO	Trace
11 ^c	CuI	K ₂S ₂O ₈	DMSO	69
12 ^d	CuI	K ₂S ₂O ₈	DMSO	44
13	CuI	TBHP	DMSO	nr
14	CuI	O ₂	DMSO	nr
15	CuI	(NH ₄) ₂S ₂O ₈	DMSO	36
16	CuI	—	DMSO	nr
17 ^e	CuI	K ₂S ₂O ₈	DMSO	42
18 ^f	CuI	K ₂S ₂O ₈	DMSO	63
19 ^g	CuI	K ₂S ₂O ₈	DMSO	77
20 ^h	CuI	K ₂S ₂O ₈	DMSO	83
21 ⁱ	CuI	K ₂S ₂O ₈	DMSO	<10

Entry	Catalyst	Oxidant	Solvent	Yield ^b /%
1	CuBr	K ₂S ₂O ₈	DMF	37
2	CuBr	K ₂S ₂O ₈	DMA	23
3	CuBr	K ₂S ₂O ₈	DMSO	67
4	CuBr	K ₂S ₂O ₈	NMP	nr
5	Cu(OAc) ₂	K ₂S ₂O ₈	DMSO	34
6	CuCl ₂	K ₂S ₂O ₈	DMSO	38
7	CuBr ₂	K ₂S ₂O ₈	DMSO	41
8	CuCl	K ₂S ₂O ₈	DMSO	58
9	CuI	K ₂S ₂O ₈	DMSO	76
10	—	K ₂S ₂O ₈	DMSO	Trace
11 ^c	CuI	K ₂S ₂O ₈	DMSO	69
12 ^d	CuI	K ₂S ₂O ₈	DMSO	44
13	CuI	TBHP	DMSO	nr
14	CuI	O ₂	DMSO	nr
15	CuI	(NH ₄) ₂S ₂O ₈	DMSO	36
16	CuI	—	DMSO	nr
17 ^e	CuI	K ₂S ₂O ₈	DMSO	42
18 ^f	CuI	K ₂S ₂O ₈	DMSO	63
19 ^g	CuI	K ₂S ₂O ₈	DMSO	77
20 ^h	CuI	K ₂S ₂O ₈	DMSO	83
21 ⁱ	CuI	K ₂S ₂O ₈	DMSO	<10

铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction

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铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

Copper-Catalyzed Three-Component Synthesis of Quinolines via Oxidation and Aza-Diels-Alder Reaction

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Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction