Copper-Catalyzed Chan-Lam Reaction and Sequential Oxidative Fischer Indole Synthesis to Prepare Indole Derivatives.

A variety of α-quinazolin-4-yloxy ketones were prepared in moderate to excellent yields through a copper-catalyzed Chan-Lam reaction/[3,3]-rearrangement of N3-hydroxyquinazolinones and alkenyl boronic acids. More importantly, α-quinazolin-4-yloxy ketones could serve as indole precursors through the Fischer indole synthesis procedure by reacting with arylhydrazines in air, which involved nucleophilic substitution, oxidation, and [3,3]-rearrangement in a one-pot. The present cascade reaction highlights a broad substrate scope, good functional group compatibility, and high rearrangement selectivity, and the obtained α-quinazolin-4-yloxy ketones served as high site-marked indole precursors.