Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone

doi:10.6023/cjoc202405001

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3375-3385.DOI: 10.6023/cjoc202405001 Previous Articles Next Articles

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光促进1,4-萘醌的一锅三组分胺基芳基化反应研究

王斌^a^,^b^,^*(), 韩万仓^b, 张永红^b, 夏昱^b, 金伟伟^b, 陈子仁^b, 武少峰^b, 刘晨江^b^,^*()

a 新疆大学分析测试中心乌鲁木齐 830017
b 新疆大学化学学院碳基能源化学与利用国家重点实验室石油天然气精细化工教育部暨自治区重点实验室乌鲁木齐绿色催化与合成技术重点实验室乌鲁木齐 830017

收稿日期:2024-05-04 修回日期:2024-06-07 发布日期:2024-07-10
基金资助:
国家自然科学基金(21762041); 国家自然科学基金(21861036); 国家自然科学基金(21961037); 新疆维吾尔自治区自然科学基金(2023B02008-3); 新疆维吾尔自治区自然科学基金(2022E01042); 新疆维吾尔自治区自然科学基金(2022TSYCCX0024); 新疆维吾尔自治区自然科学基金(2021D01E10)

Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone

Bin Wang^a^,^b,*(), Wancang Han^b, Yonghong Zhang^b, Yu Xia^b, Weiwei Jin^b, Ziren Chen^b, Shaofeng Wu^b, Chenjiang Liu^b,*()

a Analysis and Testing Center, Xinjiang University, Urumqi 830017
b Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017

Received:2024-05-04 Revised:2024-06-07 Published:2024-07-10
Contact: *E-mail:wangbin_284992269@126.com;pxylcj@126.com
Supported by:
National Natural Science Foundation of China(21762041); National Natural Science Foundation of China(21861036); National Natural Science Foundation of China(21961037); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2023B02008-3); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2022E01042); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2022TSYCCX0024); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2021D01E10)

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Abstract

1,4-Naphthoquinone, as a core skeleton exists in many bioactive molecules and has a wide range of applications in medicine, biology, cosmetics, and other synthetic materials. A photochemically synthetic method for aminoaryl bifunctionalized 1,4-naphthoquinone compounds by using 1,4-naphthoquinone, amine, and aryl triazene as raw materials is developed. This method features the advantages of simple and easy to operate without the need for any metals, extra oxidants, or other additives. It only requires methanol as the solvent and purple LED irradiation to efficiently synthesize aminoarylated 1,4- naphthoquinone derivatives. The smooth progress of gram scale reactions further proves the practicality of this method.

Key words: light promotion, one-pot three component, 1,4-naphthoquinone, aminoarylation

Cite this article

Bin Wang, Wancang Han, Yonghong Zhang, Yu Xia, Weiwei Jin, Ziren Chen, Shaofeng Wu, Chenjiang Liu. Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3375-3385.

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Entry	2a	3a	Light source	Solvent	Yield/%
1	0.35	0.2	Purple LED	MeOH	35
2	0.35	0.2	Purple LED	EtOH	Trace
3	0.35	0.2	Purple LED	DMSO	0
4	0.35	0.2	Purple LED	DCE	0
5	0.35	0.2	Purple LED	THF	Trace
6	0.4	0.2	Purple LED	MeOH	33
7	0.5	0.2	Purple LED	MeOH	38
8	0.6	0.2	Purple LED	MeOH	41
9	0.6	0.25	Purple LED	MeOH	58
10	0.6	0.35	Purple LED	MeOH	64
11	0.6	0.4	Purple LED	MeOH	73
12	0.6	0.5	Purple LED	MeOH	66
13	0.6	0.4	Blue LED	MeOH	18
14	0.6	0.4	White LED	MeOH	Trace
15	0.6	0.4	Purple LED	MeOH	63^b, 74^c, 73^d
16	0.6	0.4	—	MeOH	0

Entry	2a	3a	Light source	Solvent	Yield/%
1	0.35	0.2	Purple LED	MeOH	35
2	0.35	0.2	Purple LED	EtOH	Trace
3	0.35	0.2	Purple LED	DMSO	0
4	0.35	0.2	Purple LED	DCE	0
5	0.35	0.2	Purple LED	THF	Trace
6	0.4	0.2	Purple LED	MeOH	33
7	0.5	0.2	Purple LED	MeOH	38
8	0.6	0.2	Purple LED	MeOH	41
9	0.6	0.25	Purple LED	MeOH	58
10	0.6	0.35	Purple LED	MeOH	64
11	0.6	0.4	Purple LED	MeOH	73
12	0.6	0.5	Purple LED	MeOH	66
13	0.6	0.4	Blue LED	MeOH	18
14	0.6	0.4	White LED	MeOH	Trace
15	0.6	0.4	Purple LED	MeOH	63^b, 74^c, 73^d
16	0.6	0.4	—	MeOH	0

光促进1,4-萘醌的一锅三组分胺基芳基化反应研究

Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone

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