Metal-Free Synthesis of Benzimidazo[1,2-<i>c</i>]quinazolines from <i>N</i>-Cyanobenzimidazoles via Double C—H Functionalizations
Tian Xiaojing, Zhenzhen Fan, Si Jiang, Zhiwei Li, Jiang‐Sheng Li, Zhang Yuefei, Cui‐Hong Lu, Liu Weidong
Abstract
A green and efficient method for synthesis of privileged benzimidazo[1,2-c]quinazoline scaffolds is developed through the double C-H functionalizations mediated by peroxides under metal-free conditions without any additives. This protocol undergoes a radical cascade cyclization process involving the relay between C-centered radicals and N-centered radicals and is well applicable to a variety of cyclic (thio)ethers, glycol ethers and cyclic alkanes. Noteworthily, the title compounds display significant insecticidal and fungicidal activities, especially to armyworm.
Topics & Concepts
ChemistryStereochemistryMedicinal chemistryCombinatorial chemistryCatalytic C–H Functionalization MethodsQuinazolinone synthesis and applicationsSynthesis and Catalytic Reactions