Iodine-Mediated C═C Double Bond Cleavage toward Pyrido[2,1-<i>b</i>]quinazolinones
Wei Hao, Kailu Li, Chenyang Ye, Wenquan Yu, Junbiao Chang
Abstract
A transition-metal-free C═C double bond cleavage reaction employing molecular iodine is described. In the presence of K2CO3 as the base, I2-mediated C═C bond cleavage followed by intramolecular annulation of N-(2-vinylaryl)pyridin-2-amine substrates produces pyrido[2,1-b]quinazolinones and related heterocyclic compounds. This reaction can be completed on a gram scale and has been successfully applied to the synthesis of compounds with important biological properties, including efflux pump inhibitory and antiallergic activities.
Topics & Concepts
ChemistryIntramolecular forceAnnulationCleavage (geology)Bond cleavageAmine gas treatingIodineCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisGeotechnical engineeringEngineeringFracture (geology)Quinazolinone synthesis and applicationsSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic Chemistry