Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones.

Org Lett

College of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, State Key Laboratory of Coking Coal Resources Green Exploitation, Zhengzhou University, Zhengzhou 450052, P. R. China.

Published: December 2024

A visible-light-induced radical cyclization of α-brominated amides has been developed to construct benzimidazole[2,1-]isoquinolin-6(5)-ones and pyrrolidonesin in yields up to 97%. The methodology exhibits a certain functional-group compatibility with 43 examples and operational simplicity, offering a rapid and concise approach to obtain five- and six-membered rings under the irradiation of 18 W blue LED. Additionally, large-scale reaction of this method for synthesizing benzimidazo-isoquinolineones and the further transformations to useful pyrrolidones were also conducted and afforded positive results.

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http://dx.doi.org/10.1021/acs.orglett.4c04292DOI Listing

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