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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

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
› Author AffiliationsWe 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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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

    Supporting information for this article is available online at https://doi.org/10.1055/a-1890-7743.
  • 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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