The reactions of hydrazones and related compounds with strong bases. Part 4. 4,5-Diaryl-1,2,3-triazoles from aromatic aldehyde azines and from the reaction of arenecarbonitriles with aryldiazomethanes

Abstract

Reaction of aromatic aldehyde azines in dimethyl sulphoxide at 20 °C with potassium t-butoxide gave 4,5-diaryl-1,2,3-triazoles (4) and stilbenes. Mechanisms were studied by addition of possible intermediates and by ¹⁴C tracer methods. The synthesis of 4,5-diaryl-1,2,3-triazoles from arenecarbonitriles, aryldiazomethanes, and potassium t-butoxide in toluene is described and the mechanism is discussed.