Synthesis of 1-alkyl-4(5)-hydroxymethyl-1,2,3-triazoles

Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne–Azide Cycloaddition of Inorganic Azides

“…An early example is the cycloaddition of hydrazoic acid to acetylene, which upon heating yields un-substituted NH-1,2,3-triazole. 1 The reluctant reactivity of sodium azide with alkynes, due to a large activation enthalpy 2 , is the basis of the success of the one-pot, two-step synthesis scheme 3,4 in which sodium azide first reacts with an organic halide, yielding an organic azide that in a second step reacts with an alkyne via a Cu(I)-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) reaction to generate the desired triazole, often in high yield. However, it was also noted that if the nucleophilic substitution of the halide is inefficient, then formation of an NH-triazole can occur as an undesired side reaction.…”

Multicomponent Syntheses based upon Copper‐Catalyzed Alkyne‐Azide Cycloaddition

“…[24] Later Blass et al reported a one-pot, two step synthesis of functionalized 1,2,3triazoles via alkyl halides and alkynes using polymersupported azides under thermal cycloaddition conditions. [24] Later Blass et al reported a one-pot, two step synthesis of functionalized 1,2,3triazoles via alkyl halides and alkynes using polymersupported azides under thermal cycloaddition conditions.…”

“…Already for the thermal azide‐alkyne cycloaddition, the in situ formation of azides for the synthesis of the corresponding triazoles was taken into account although low yields and poor regioselectivities were obtained as a consequence of long reaction times at higher temperatures 24. Later Blass et al reported a one‐pot, two step synthesis of functionalized 1,2,3‐triazoles via alkyl halides and alkynes using polymer‐supported azides under thermal cycloaddition conditions 25.…”

Silica Functionalized Cu(I) as a Green and Recyclable Heterogeneous Catalyst for the Huisgen 1,3-Dipolar Cycloaddition in Water at Room Temperature

“…In situ generation of organic azides from suitable precursors followed by addition of alkyne in one-pot, to form the corresponding 1,2,3-triazole would avoid the difficulties associated with the explosive nature of azides. Recently, copper catalyzed one-pot synthesis of 1,2,3-triazoles from aryl/alkyl halides, alkynes and sodium azides have been reported [26]. However, these homogeneous processes suffer from one or more disadvantages like, difficulty in separation of the product from the reaction medium, catalysts are generally non-recyclable, low regioselectivity and long reaction times.…”