Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light

doi:10.6023/cjoc202110022

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1210-1215.DOI: 10.6023/cjoc202110022 Previous Articles Next Articles

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紫外光引发胺基苯酚与胺的自由基偶联反应构筑二胺基苯醌亚胺类化合物

许丽梅^a, 卢林燕^a, 蔡尽忠^a, 冯亚栋^a^,^b^,^*(), 崔秀灵^b^,^*()

a 厦门华厦学院环境与公共健康学院福建厦门 361024
b 华侨大学生物医学学院分子药物教育部工程研究中心福建省分子医学重点实验室福建省高校精准医学与分子诊断重点实验室厦门市海洋与基因药物重点实验室福建厦门 361021

收稿日期:2021-10-15 修回日期:2021-11-17 发布日期:2021-12-02
通讯作者: 冯亚栋, 崔秀灵
基金资助:
福建省中青年教师教育科研(JAT190990)

Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light

Limei Xu^a, Linyan Lu^a, Jinzhong Cai^a, Yadong Feng^a^,^b(), Xiuling Cui^b()

a College of Environment and Public Health, Xiamen Huaxia University, Xiamen, Fujian 361024
b Engineering Research Center of Molecular Medicine, Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen, Fujian 361021

Received:2021-10-15 Revised:2021-11-17 Published:2021-12-02
Contact: Yadong Feng, Xiuling Cui
Supported by:
Fujian Education and Scientific Research Project for Young and Middle-Aged Teachers(JAT190990)

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Abstract

A metal-free radical coupling reaction of aminophenols with amines under UV-light has been successfully developed to synthesize diaminobenzoquinone imines in high yields, in which the commercially available and cheap t-butyl hydroperoxide (TBHP) was used as an oxidant. This protocol provides an easy and green approach for the construction of benzoquinone imines with potential pharmaceutical interest avoiding metal catalyst or photocatalyst.

Key words: UV-light, radical coupling, metal-free, diaminobenzoquinone imines

Cite this article

Limei Xu, Linyan Lu, Jinzhong Cai, Yadong Feng, Xiuling Cui. Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1210-1215.

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References 11

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紫外光引发胺基苯酚与胺的自由基偶联反应构筑二胺基苯醌亚胺类化合物

Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light

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Entry	UV-light (λ_max, P)	TBHP/ equiv.	Solvent	T/℃
1	365 nm, 250 W	3.0	Toluene	80	85
2	—	3.0	Toluene	80	35
3^c	365 nm, 250 W	3.0	Toluene	80	82
4^d	365 nm, 250 W	3.0	Toluene	80	85
5	365 nm, 200 W	3.0	Toluene	80	71
6	365 nm, 150 W	3.0	Toluene	80	62
7	365 nm, 250 W	—	Toluene	80	21
8	365 nm, 250 W	2.0	Toluene	80	51
9	365 nm, 250 W	1.0	Toluene	80	30
10	365 nm, 250 W	4.0	Toluene	80	96
11	365 nm, 250 W	5.0	Toluene	80	96
12	365 nm, 250 W	6.0	Toluene	80	92
13	365 nm, 250 W	4.0	DMSO	80	Trace
14	365 nm, 250 W	4.0	DMF	80	33
15	365 nm, 250 W	4.0	NMP	80	65
16	365 nm, 250 W	4.0	Dioxane	80	61
17	365 nm, 250 W	4.0	CH₃OH	80	Trace
18	365 nm, 250 W	4.0	CH₃CN	80	27
19	365 nm, 250 W	4.0	Toluene	90	89
20	365 nm, 250 W	4.0	Toluene	70	86
21^e	365 nm, 250 W	4.0	Toluene	80	95
22^f	365 nm, 250 W	4.0	Toluene	80	87