Facile synthesis of Bis(1,2,3-triazole) and 1,1’-azobis-1,2,3-triazole via divergent one-step oxidation of glyoxal dihydrazone

Here we present a novel divergent one-step oxidation strategy for the synthesis of bis(1,2,3-triazole) and 1,1'-azobis-1,2,3-triazole using readily available glyoxal dihydrazone as the starting material. Using MnO2 as the oxidant, bis(1,2,3-triazole) could be obtained in 50% yield employing CCl4 as solvent at 18°C. Changing the oxidant to KMnO4 and the solvent to CH2Cl2 produced 1,1'-azobis-1,2,3-triazole as the main product. This provides an efficient strategy for the generation of bis(1,2,3-triazole) and 1,1'-azobis-1,2,3-triazole. We propose that this approach may be used for the construction of other long N-chain structures.