Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues
Chao Liu, Adriano Bolognani, Liangliang Song, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van der Eycken
Abstract
A gold(I)-catalyzed cascade intramolecular cyclization of Ugi adducts for the divergent construction of quinazolinone and ampakine analogues has been developed in a rapid, highly efficient and step-economical manner. This protocol shows high yields, excellent functional-group tolerance, broad substrate scope and excellent chemo- and regioselectivity. The practicality of this strategy is further demonstrated by a scale-up reaction. Diverse oligopeptides are also found to be well tolerated, affording polycyclic products decorated with a peptide chain.
Topics & Concepts
QuinazolinoneChemistryIntramolecular forceRegioselectivityCombinatorial chemistryCatalysisAdductSubstrate (aquarium)Functional groupStereochemistryOrganic chemistryPolymerOceanographyGeologyCatalytic Alkyne ReactionsChemical Synthesis and AnalysisQuinazolinone synthesis and applications