Gold(I)-Catalyzed Intramolecular Bicyclization: Divergent Construction of Quinazolinone and Ampakine Analogues

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.

Automated summary

A gold(I)-catalyzed cascade intramolecular cyclization of Ugi adducts has been developed for the divergent construction of quinazolinone and ampakine analogues in a rapid, efficient and step-economical manner. This method 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.