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

Abstract : The mechanochemical synthesis of 1,2,4-triazoles by using a planetary ball-mill is studied starting from hydralazine hydrochloride. Excellent conditions were found for achieving total conversion to intermediate hydrazones in a few minutes in the presence of pyrogenic S13 silica as grinding auxiliary. The conversion to annulated 1,2,4-triazoles was optimal with iodobenzene diacetate (IBD) when using nonphenolic 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 syntheses of hydrazone 10 and triazole 13.
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Submitted on : Saturday, March 28, 2020 - 4:07:01 PM
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Lori Gonnet, Christiane André-Barrès, Brigitte Guidetti, Alain Chamayou, Christophe Menendez, et al.. Study of the Two Steps and One-Pot Two-Step Mechanochemical Synthesis of Annulated 1,2,4-Triazoles. ACS Sustainable Chemistry & Engineering, American Chemical Society, 2020, 8 (8), pp.3114-3125. ⟨10.1021/acssuschemeng.9b05886⟩. ⟨hal-02519781⟩



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