Solid-Phase Synthesis of 1,2,3-Triazoles via 1,3-Dipolar Cycloaddition

Abstract

The solid-phase synthesis of 1,2,3-triazoles via 1,3-dipolar cycloaddition of polymer-bound azides to various alkynes is reported. Polymer-bound azides were synthesized from polymer-bound halides and sodium azide and reacted with alkynes to produce polymer-bound 1,2,3-triazoles. Cleavage of the triazoles was performed with trifluoroacetic acid. A traceless synthesis of 1,2,3-triazoles was developed using 2-methoxy-substituted resin (polymer-bound 4-hydroxy-2-methoxybenzyl alcohol). In addition, a synthesis of 4-hydroxybenzyl-substituted 1,2,3-triazoles from the bromo-Wang resin (4-(bromomethyl)phenoxymethyl polystyrene) was achieved.

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…Functionalized 1,2,3-triazoles 26 and 27 were prepared by [3 þ 2] cycloaddition of resin-bound a-azido esters 25 with terminal alkynes (Scheme 12.12) [57]. Polystyrene resin-bound azide 28 reacted with disubstituted alkynes followed by acidic cleavage to give 1,2,3-triazoles 29 (Scheme 12.13) [58]. 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].…”

Analysis of small molecules by ultra thin-layer chromatography-atmospheric pressure matrix-assisted laser desorption/ionization mass spectrometry

“…The reference standards of midazolam, verapamil (as hydrochloride salt) and metoprolol (as tartrate salt) were obtained from Roche (Basel Switzerland), Sigma-Aldrich (Steinheim, Germany), and ICN Biomedicals (Aurora, OH), respectively. Five other compounds, which all are 1,2,3-triazoles (Figure 1), were selected from a combinatorial library synthesized in our laboratory by the solid-phase method described by Harju et al [40]. ␣-Cyano-4-hydroxycinnamicëacid (␣-CHCA), used as a matrix compound for MALDI-MS analysis, was purchased from Fluka Chemie (Buchs, Switzerland).…”

Glycosylated cell-penetrating peptides and their conjugates to a proapoptotic peptide: preparation by click chemistry and cell viability studies

“…It is worth noting that these conditions are not detrimental to the carbohydrate and the triazole link [39,40]. The reproducibility and sensitivity of IR analysis (alkyne signal at 2,200 cm −1 ) was not sufficient to monitor the reaction by taking aliquots of the resin [41,42]. Azidorhodamine analog 9 (refer to Supplementary files), prepared from rhodamine B, exhibited fluorescence quenching (approximately ten times) when covalently linked via a triazole to the solid support, as previously reported [43].…”