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Synthesis 2022; 54(23): 5233-5244
DOI: 10.1055/a-1890-7743
paper

Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions

Authors

  • Li-Lin Jiang

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Ling-Tao Wang

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Hui Qiu

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Fa-Liang Liu

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Xun-Jie Huang

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Ting-Ting Cao

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Guo-Ping Ge∗

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

  • Yi-Lin Liu∗

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China
    b   College of Chemistry and Materials Engineering, Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA) Fiber Material, Huaihua University, Huaihua, Hunan 418008, P. R. of China

  • Wen-Ting Wei∗

    a   Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, P. R. of China

We thank the Fundamental Research Funds for the Provincial Universities of Zhejiang (SJLY2021004), Education Foundation of Zhejiang Province (Nos. Y202148290; Y202146200), and the Natural Science Foundation of Hunan Province (No. 2020JJ5448).
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Graphical Abstract

Abstract

A method for radical cyclization of N-methacryloyl-2-arylbenzoimidazoles with nitriles, ketones, and tert-butyl nitrite (TBN) for the preparation of benzimidazo[2,1-a]isoquinolin-6(5H)-ones with the advantage of mild reaction conditions, excellent functional group compatibility, and broad substrate scope is reported. The present strategy has favorable characteristics: (1) the use of cheap metal catalysis; (2) N-radical-initiated cyclization of N-methacryloyl-2-arylbenzoimidazoles; and (3) rare example of radical C(sp3)–H functionalization in this cyclization.

Key words

green synthesis - cheap metal catalysis - C(sp3)–H functionalization - radical cyclization

Supporting Information



Publication History

Received: 25 May 2022

Accepted after revision: 03 July 2022

Accepted Manuscript online:
03 July 2022

Article published online:
22 August 2022

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