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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 9: 3682 - 3691

DOI: https://doi.org/10.6023/cjoc202104005

ARTICLES

NEt3-Promoted Construction of Functionalized 4H-Chromenes via [4+2] Cycloaddition Reaction of ortho-Quinone Methides with β-Ketothioamides

  • Guangming Nan ,
  • Jingbo Zhan ,
  • Chunming Yuan ,
  • Lirong Wen ,
  • Ming Li
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  • a University and College Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining, Xinjiang 835000
    b State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, Sahndong 266042
* Corresponding authors. E-mail: ;

Received date: 2021-04-02

  Revised date: 2021-05-26

  Online published: 2021-06-17

Supported by

National Natural Science Foundation of China(21572110); Natural Science Foundation of Shandong Province(ZR2019MB010)

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Abstract

A novel and efficient method for the synthesis of highly substituted 4H-chromene derivatives by NEt3-promoted annulation of β-ketothioamides (KTAs) and ortho-quinone methides (o-QMs) has been developed. This protocol involves a tandem sequence including 1,6-conjugate addition/O-cyclization/ring-opening/O-cyclization. This process exhibits good functional group tolerance, operationally-simple conditions and scalability.

Key words： ortho-quinone methide (o-QMs); β-ketothioamide; 4H-chromene derivative; [4+2] cycloaddition

Cite this article

Guangming Nan , Jingbo Zhan , Chunming Yuan , Lirong Wen , Ming Li . NEt3-Promoted Construction of Functionalized 4H-Chromenes via [4+2] Cycloaddition Reaction of ortho-Quinone Methides with β-Ketothioamides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(9) : 3682 -3691 . DOI: 10.6023/cjoc202104005

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