1,3-Dipolar cycloaddition of benzyl azide to two highly functionalized alkynes

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

“…Scheme 10. CuAAC and attempted RuAAC using highly functionalized alkynes 85 Piperidines are common motifs in natural products as well as in pharmaceuticals. Haug and colleagues prepared a set of 3-hydroxypiperidine triazoles using both CuAAC and RuAAC.…”

A-21·CuI as a catalyst for Huisgen’s reaction: about iodination as a side-reaction

“…Addition of haloreagents such as NBS and NCS in stoichiometric amounts in CuAAC gave good yields of the iodinated triazole. 15 However, in Table 2 Reactions of alkynes 2 and 3 with benzyl azide (1) Table 2).…”

Synthesis and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties

“…For the synthesis of target compounds, solution of aromatic bromides (1.0 mmol) in dimethylformamide was taken in a round-bottomed flask and aqueous solution of sodium azide (3.0 mmol) was added, thereafter, stirred the reaction mixture for 1 h at 25-40°C. To the above reaction mixture, benzofused N-heteroaromatic alkyne 2 (1.0 mmol), 5 (1.0 mmol), or 8 (1.0 mmol) was added followed by copper sulfate pentahydrate (5 mol %) and sodium ascorbate (10 mol %) [33], then, stirred the reaction contents overnight. The progress of reaction was monitored by thin layer chromatography.…”

“…The benzofused N-heteroaromatic alkynes were synthesized [32] by reacting benzimidazole, benzotriazole, or carbazole with propargyl bromide in the presence of potassium carbonate in dimethylformamide at ambient temperature. 1,4-Disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties were synthesized via click reaction of benzofused N-heteroaromatic alkynes with aromatic azides which in turn were prepared by in situ reaction of aromatic bromides with sodium azide, as per literature procedure [33].…”