Indium-mediated annulation of 2-azidoaryl aldehydes with propargyl bromides to [1,2,3]triazolo[1,5-a]quinolines

Abstract

An efficient indium-mediated cascade annulation reaction of 2-azidoaryl aldehydes with propargyl bromides is reported. The aromatic 5/6/6-fused heterocycles, [1,2,3]triazolo[1,5-a]quinoline derivatives, could be constructed in one pot in moderate yields with a broad substrate scope. Mechanistic studies indicated that the reaction proceeded through allenol formation, azide–allene [3 + 2] cycloaddition, and dehydration. The synthetic potential of the products including the denitrogenative functionalization and the Pd-catalyzed coupling reactions has also been explored.