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The mechanochemical synthesis of 1,2,4-triazoles by using a planetary ball-mill is studied starting from hydralazine hydrochloride. Excellent conditions for achieving total conversion to intermediate hydrazones in a few minutes in the presence of pyrogenic S13 silica as grinding auxiliary were found. The conversion to the annulated 1,2,4-triazoles was optimal with iodobenzene diacetate (IBD) when using non-phenolic hydrazones, while SeO2 was found to be efficient for phenolic compounds. The one-pot two-step synthesis was also successfully conducted for the first time leading to annulated 1,2,4-triazoles. Finally, green metrics showed the efficiency of the method in comparison to the conventional synthesis of hydrazone 10 and triazole 13.

Study of the Two Steps and One-Pot Two-Step Mechanochemical Synthesis of Annulated 1,2,4-Triazoles