On March 18, 2022, Jankovic, Dominik; Virant, Miha; Gazvoda, Martin published an article.Category: triazoles The title of the article was Copper-Catalyzed Azide-Alkyne Cycloaddition of Hydrazoic Acid Formed In Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles. And the article contained the following:
Authors report a copper-catalyzed cycloaddition of hydrogen azide (hydrazoic acid, HN3) with terminal alkynes to form 4-substituted-1,2,3-triazoles in a sustainable manner. Hydrazoic acid was formed in situ from sodium azide under acidic conditions to react with terminal alkynes in a copper-catalyzed reaction. Using polydentate N-donor chelating ligands and mild organic acids, the reactions were realized to proceed at room temperature under aerobic conditions in a methanol-water mixture and with 5 mol % catalyst loadings to afford 4-substituted-1,2,3-triazoles in high yields. This method is amenable on a wide range of alkyne substrates, including unprotected peptides, showing diverse functional group tolerance. It is applicable for late-stage functionalization synthetic strategies, as demonstrated in the synthesis of the triazole analog of losartan. The preparation of orthogonally protected azahistidine from Fmoc-L-propargylglycine was realized on a gram scale. The hazardous nature of hydrazoic acid has been diminished as it forms in situ in <6% concentrations at which it is safe to handle. Reactions of distilled solutions of hydrazoic acid indicated its role as a reactive species in the copper-catalyzed reaction. The experimental process involved the reaction of 4-(p-Tolyl)-1H-1,2,3-triazole(cas: 5301-96-2).Category: triazoles
The Article related to triazole preparation green chem, azide alkyne cycloaddition copper, Heterocyclic Compounds (More Than One Hetero Atom): Other 5-Membered Rings, Two Or More Hetero Atoms and other aspects.Category: triazoles
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics