Click Reaction of Calcium Carbide-Derived Acetylene as a Direct Way to Chromophore- and Fluorophore-Substituted 1,2,3-Triazoles

Abstract

1-[4-(Phenyldiazenyl)phenyl]-1H-1,2,3-triazole and 3-(1H-1,2,3-triazol-1-yl)-2H-chromen-2-one were synthesized for the first time by using the copper-catalyzed azide-alkyne cycloaddition reaction of azobenzene- and coumarin-substituted azides and calcium carbide-derived acetylene. Both azobenzene- and coumarin-substituted substrates afforded target 1,2,3-triazoles in good yields by reacting with acetylene generated from calcium carbide and water directly in the reaction vessel. This work demonstrates the enhanced applicability of the calcium carbide approach in organic synthesis, including the synthesis of chromophore- and fluorophore-substituted compounds.