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The construction of benzimidazo[2,1-a]isoquinolin-6(5H)-ones from N-methacryloyl-2-phenylbenzoimidazoles through radical strategies
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-09-16 , DOI: 10.1039/d1ob01465j Qing-Qing Kang 1 , Wei-Kang Zhang 1 , Guo-Ping Ge 1 , Hongxing Zheng 2 , Wen-Ting Wei 1
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-09-16 , DOI: 10.1039/d1ob01465j Qing-Qing Kang 1 , Wei-Kang Zhang 1 , Guo-Ping Ge 1 , Hongxing Zheng 2 , Wen-Ting Wei 1
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Benzimidazo[2,1-a]isoquinolin-6(5H)-one constitutes a structurally unique class of tetracyclic N-heterocycles that are found throughout a myriad of biologically active natural products, pharmaceutical compounds, and functional materials. Various synthetic routes for the preparation of benzimidazo[2,1-a]isoquinolin-6(5H)-ones have been reported. In particular, the use of N-methacryloyl-2-phenylbenzoimidazoles to construct benzimidazo[2,1-a]isoquinolin-6(5H)-ones through various radical strategies have attracted widespread attention due to the versatility and simple preparation of raw materials, as well as the step-economy and mild reaction conditions. Using representative examples, we highlight significant progress in the synthesis of benzimidazo[2,1-a]isoquinolin-6(5H)-ones, including the selection of the catalytic system, substrate scope, mechanistic understanding, and applications. The contents of this review focus on the development of C-, S-, P-, and Si-centered radical addition–intramolecular cyclization strategies.
中文翻译：
N-甲基丙烯酰基-2-苯基苯并咪唑通过自由基策略构建苯并咪唑[2,1-a]异喹啉-6(5H)-ones
Benzimidazo[2,1 - a ]isoquinolin-6(5 H )-one 构成了一类结构独特的四环 N-杂环，存在于无数具有生物活性的天然产物、药物化合物和功能材料中。已报道了用于制备苯并咪唑[2,1- a ]异喹啉-6(5 H )-酮的各种合成路线。特别是利用N-甲基丙烯酰基-2-苯基苯并咪唑构建苯并咪唑并[2,1- a ]isoquinolin-6(5 H)-通过各种激进策略进行的反应由于原料的通用性和简单制备，以及分步经济和温和的反应条件而引起了广泛关注。通过具有代表性的例子，我们强调了苯并咪唑[2,1- a ]isoquinolin-6(5 H )-ones合成的重大进展，包括催化体系的选择、底物范围、机理理解和应用。本综述的内容集中在C-、S-、P-和Si中心自由基加成-分子内环化策略的发展。
更新日期：2021-10-07
中文翻译：
N-甲基丙烯酰基-2-苯基苯并咪唑通过自由基策略构建苯并咪唑[2,1-a]异喹啉-6(5H)-ones
Benzimidazo[2,1 - a ]isoquinolin-6(5 H )-one 构成了一类结构独特的四环 N-杂环，存在于无数具有生物活性的天然产物、药物化合物和功能材料中。已报道了用于制备苯并咪唑[2,1- a ]异喹啉-6(5 H )-酮的各种合成路线。特别是利用N-甲基丙烯酰基-2-苯基苯并咪唑构建苯并咪唑并[2,1- a ]isoquinolin-6(5 H)-通过各种激进策略进行的反应由于原料的通用性和简单制备，以及分步经济和温和的反应条件而引起了广泛关注。通过具有代表性的例子，我们强调了苯并咪唑[2,1- a ]isoquinolin-6(5 H )-ones合成的重大进展，包括催化体系的选择、底物范围、机理理解和应用。本综述的内容集中在C-、S-、P-和Si中心自由基加成-分子内环化策略的发展。
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