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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 12: 4798 - 4807

DOI: https://doi.org/10.6023/cjoc202106044

ARTICLES

Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides

  • Yuchao Wang ,
  • Jinbiao Liu ,
  • Guanyinsheng Qiu ,
  • Yu Yang ,
  • Hongwei Zhou
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  • a Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou, Jiangxi 341000
    b College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001
* Corresponding authors. E-mail: ;
;

Received date: 2021-06-24

  Revised date: 2021-08-22

  Online published: 2021-09-03

Supported by

National Natural Science Foundation of China(21772067); National Natural Science Foundation of China(21762018); National Natural Science Foundation of China(21961014); Natural Science Foundation of Jiangxi Province(20192BCBL23009); Natural Science Foundation of Jiangxi Province(20202BABL203005); Youth Jinggang Scholars Program in Jiangxi Province

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Abstract

Facile ipso-cyclization and regioselective ortho-capture of N-hydroxylethyl-N-arylpropiolamides are reported for the synthesis of various selenium-containing benzo[b]pyrrolo[2,1-c][1,4]oxazin-3-ones. The reaction works well with high efficiency and broad reaction scope. In the process, it is believed that α-addition of the propiolamide, sequential ipso-cyclization of the aniline, and regioselective ortho-capture with a hydroxyl group are involved.

Key words： selenization; dearomatization; ipso-cyclization; N-hydroxylethyl-N-phenylpropiolamide

Cite this article

Yuchao Wang , Jinbiao Liu , Guanyinsheng Qiu , Yu Yang , Hongwei Zhou . Metal-Free Selenizative spiro-Tricyclization of N-Hydroxylethyl-N-arylpropiolamides[J]. Chinese Journal of Organic Chemistry, 2021 , 41(12) : 4798 -4807 . DOI: 10.6023/cjoc202106044

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