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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 11: 3375 - 3385

DOI: https://doi.org/10.6023/cjoc202405001

ARTICLE

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

  • Bin Wang ,
  • Wancang Han ,
  • Yonghong Zhang ,
  • Yu Xia ,
  • Weiwei Jin ,
  • Ziren Chen ,
  • Shaofeng Wu ,
  • Chenjiang Liu
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  • 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
*Corresponding authors. E-mail:;

Received date: 2024-05-04

  Revised date: 2024-06-07

  Online published: 2024-07-10

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 . DOI: 10.6023/cjoc202405001

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