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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 11: 3866 - 3872

DOI: https://doi.org/10.6023/cjoc202007005

K2S2O8-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines

  • Chen Zhichao ,
  • Zhang Hong ,
  • Zhou Shufeng ,
  • Cui Xiuling
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  • a College of Chemical Engineering, Huaqiao University, Xiamen, Fujian 361021;
    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 date: 2020-07-01

  Revised date: 2020-07-30

  Online published: 2020-08-11

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572072) and the Programme of Introducing Talents of Discipline to Universities (111 Project, No. BC 2018061).

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Abstract

A convenient K2S2O8-initiated radical cascade cyclization for the construction of 4-sulfonated cyclopenta[gh]-phenanthridines from 2-alkynylnitriles and sodium sulfinates has been explored under metal-free conditions. This protocol features mild conditions, good functional group tolerance and broad substrate scope. A variety of potentially bioactive 4-sulfonated cyclopenta[gh]phenanthridines were facilely synthesized via direct annulation.

Key words： 2-alkynylnitriles; sodium sulfinate; 4-sulfonated cyclopenta[gh]phenanthridine; radical cyclization cascade

Cite this article

Chen Zhichao , Zhang Hong , Zhou Shufeng , Cui Xiuling . K2S2O8-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines[J]. Chinese Journal of Organic Chemistry, 2020 , 40(11) : 3866 -3872 . DOI: 10.6023/cjoc202007005

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