Copper-Catalyzed One-pot Synthesis of Amide Linked 1,2,3-Triazoles Bearing Aryloxy Skeletons

Abstract In this paper, novel amide linked 1,2,3-triazoles containing aryloxy derivatives (8a–l) are synthesized via copper-catalyzed one-pot sequential hydroxylation-O-alkylation/click reaction of 2-bromo-N-prop-2-ynyl-benzamides. The products are synthesized in an efficient way in high isolated yields. The synthetic method involves the use of 2-bromo-N-prop-2-ynyl-benzamide and various benzyl halides over a one-pot copper-catalyzed hydroxylation-O-alkylation/Click reaction. The products are characterized by 1H NMR, 13C NMR, mass spectrometry, FT-IR, elemental analysis, melting point, and single crystal X-ray diffraction. In-situ prepared phenol moiety in H2O/DMF as a solvent\co-solvent system prompted to perform a reaction between benzyl halide and phenols. The step economic feature of the method leads to the synthesis of the products in high isolated yields.