The construction of benzimidazo[2,1-a]isoquinolin-6(5H)-ones from N-methacryloyl-2-phenylbenzoimidazoles through radical strategies

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.

Automated summary

Benzimidazo[2,1-a]isoquinolin-6(5H)-one is a structurally unique class of tetracyclic N-heterocycles found in various biologically active natural products, pharmaceutical compounds, and functional materials. The use of N-methacryloyl-2-phenylbenzoimidazoles to construct benzimidazo[2,1-a]isoquinolin-6(5H)-ones through radical strategies has attracted attention due to its versatility and simple preparation of raw materials. This review highlights significant progress in the synthesis of benzimidazo[2,1-a]isoquinolin-6(5H)-ones, focusing on various radical addition-intramolecular cyclization strategies.