Metal-free tandem reactions of 2-iodoaryl ynones with sodium azide for the synthesis of benzoisoxazole containing 1,2,3-triazoles

A metal-free approach has been developed for the synthesis of benzo[c]isoxazole (anthranils) containing 1,2,3-triazoles. The reaction proceeded efficiently through a [3 + 2] azide-alkyne cycloaddition, S_NAr azidation and denitrogenative cyclization sequence. The metal-free protocol enabled effective construction of one N-O and three C-N bonds in one pot. In addition, the synthetic utility of the current methodology was further demonstrated by late stage modification of the obtained products.