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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 8: 3171 - 3179

DOI: https://doi.org/10.6023/cjoc202103027

ARTICLES

Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives

  • Sai Shu ,
  • Zhibin Huang ,
  • Yujie Chen ,
  • Shan Yang ,
  • Yaqiqi Jiang ,
  • jingyu Zhang ,
  • Yingsheng Zhao
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  • a College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
    b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453000
*Corresponding authors.E-mail: ;
E-mail:

Received date: 2021-03-16

  Revised date: 2021-04-10

  Online published: 2021-05-14

Supported by

National Natural Science Foundation of China(21772139); National Natural Science Foundation of China(21572149); Major Basic Research Project of the Natural Science Foundation of Jiangsu Higher Education Institutions(15KJA150006); Natural Science Found for Distinguished Young Scholars of Jiangsu Province(BK2018g0041); Project of Scientific and Technologic infrastructure of Suzhou(SZS2018201708); Open Foundation of Backbone Characteristic Discipline of Chemistry of Henan Normal University; Priority Academic Program Development of Jiangsu Higher Education Institutions

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Abstract

A Rh(III)-catalyzed, regioselective C(2)—H activation/cyclization of N-methoxy-1H-indole-1-carboxamides and sulfoxonium ylides was developed. This novel synthetic procedure afforded dihydropyrimido[1,6-a]indol-1(2H)-ones in moderate to excellent yields. This reaction proceeds under simple and mild conditions with low catalyst loading and tolerates a wide range of substrates.

Key words： indoles; sulfoxonium ylides; cyclization

Cite this article

Sai Shu , Zhibin Huang , Yujie Chen , Shan Yang , Yaqiqi Jiang , jingyu Zhang , Yingsheng Zhao . Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3171 -3179 . DOI: 10.6023/cjoc202103027

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