Trimethylsilyl-Directed 1,3-Dipolar Cycloaddition Reactions in the Solid-Phase Synthesis of 1,2,3-Triazoles

Abstract

[reaction: see text] A regioselective method for the preparation of 1,5-trisubstituted 1H-1,2,3-triazoles via a 1,3-dipolar cycloaddition of 1-trimethylsilylacetylenes with organoazides is described. Immobilization of the azide on REM resin and subsequent cycloaddition afforded a 2 x 2 x 4 x 3 membered 1,5-disubstituted 1H-1,2,3-triazole library with an average purified yield of 68%.

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Although there are numerous studies on CuAAC functionalization of nonporous polymers [280,298,328,[336][337][338][339][340][341][342][343][344][345][346][347][348][349][350][351], silica [352][353][354] and metal particles [355], the amount of publications on porous polymer particles is limited. Finn et al [356] described the click functionalization of a commercial porous agarose resin for affinity chromatography.…”

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…Regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of resin-bound alkynes 30 to azides afforded solid-supported 1,2,3-triazoles 31, which were ligated further to give 1,4-substituted-1,2,3-triazole-peptide compounds (Scheme 12.14) [59]. Immobilized REM resin azides have provided a regioselective method for the preparation of 1,5-trisubstituted-1H-1,2,3-triazoles via a 1,3-dipolar cycloaddition of trimethylsilyl-propynoic acid [60]. A library of peptidotriazoles have been prepared by solid-phase peptide synthesis combined with a regiospecific copper (I)-catalyzed 1,3-dipolar cycloaddition between resin-bound alkynes and protected amino azides [61].…”

Water as a promoting media for 1,3-dipolar cycloaddition of phosphorylated azides to internal alkynes

“…For example, 1,3-dipolar cycloaddition of organic azides to 1-trimethylsilyl carbalkoxy-acetylenes was completed over 14 h in refluxing toluene, 16 alkynes. For alkynes of both types the reactions were carried out in the presence of different catalysts and only a few publications reported on cycloaddition without any additives (in three cases of four DMAD was used as an alkyne).…”