Synthesis of Fully Substituted 5-(<i>o</i>-Hydroxybenzoyl)imidazoles via Iodine-Promoted Domino Reaction of Aurones with Amidines
Hui Xu, Hong Chen, Xiao Hu, Guang Xuan, Pinhua Li, Ze Zhang
Abstract
An iodine-promoted domino reaction of aurones with amidines has been successfully explored. The reaction proceeds in a consecutive manner containing Michael addition, iodination, cyclization from intramolecular nucleophilic substitution, and dehydrogenative aromatization from spiro ring opening. Following this novel strategy, a variety of 1,2,4-trisubstituted 5-(o-hydroxybenzoyl)imidazoles were efficiently synthesized in moderate to good yields from readily available starting materials. A plausible mechanism has been proposed.
Topics & Concepts
ChemistryIodineIntramolecular forceAromatizationDominoNucleophilic substitutionHalogenationRing (chemistry)Medicinal chemistryOrganic chemistryCombinatorial chemistryCatalysisSynthesis of Organic CompoundsMulticomponent Synthesis of HeterocyclesOxidative Organic Chemistry Reactions