Radical Cyclization of N-Methacryloyl-2-arylbenzoimidazoles with Nitriles, Ketones, and tert-Butyl Nitrite under Mild Conditions-Reference-Cited by-同舟云学术

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

Published:2022-07-03 Issue:23 Volume:54 Page:5233-5244
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Ge Guo-Ping¹,Liu Yi-Lin¹²,Wei Wen-Ting¹,Jiang Li-Lin¹,Wang Ling-Tao¹,Qiu Hui¹,Liu Fa-Liang¹,Huang Xun-Jie¹,Cao Ting-Ting¹

Affiliation:

1. Institute of Drug Discovery Technology, School of Materials Science and Chemical Engineering, Ningbo University

2. College of Chemistry and Materials Engineering, Hunan Engineering Laboratory for Preparation Technology of Polyvinyl Alcohol (PVA) Fiber Material, Huaihua University

Abstract

AbstractA 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.

Funder

Department of Education of Zhejiang Province

Natural Science Foundation of Hunan Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1890-7743.pdf

Reference4 articles.

1. Oxidative Radical Relay Functionalization for the Synthesis of Benzimidazo[2,1‐ a ]iso‐quinolin‐6(5 H )‐ones

2. Selective divergent radical cyclization of 1,6-dienes with alkyl nitriles

3. Iron-catalyzed oxidative cyclization of olefinic 1,3-dicarbonyls with ketone C(sp3)–H bonds: facile access to 2,3-dihydrofurans

4. Radical Cyclization of Olefinic Amides through α-C(sp3)–H Functionalization of Ketones under Catalyst-, Ligand-, and Base-Free Conditions

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