One-Pot Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from In Situ Generated Azides

Abstract

[reaction: see text] 1,4-Disubstituted 1,2,3-triazoles are obtained in excellent yields by a convenient one-pot procedure from a variety of readily available aromatic and aliphatic halides without isolation of potentially unstable organic azide intermediates.

Liquid-phase synthesis of 4-vinyl-1H-1,2,3-triazoles based on polyethylene glycol supported but-3-ynyl sulfonate

“…14 There are, however, only a few reports concerning the synthesis of vinyl-substituted 1,2,3-triazoles. [15][16][17][18][19] Even up to now, only a few methods for preparation of some typical vinyl-substituted As shown in Scheme 1, treatment of the difunctionalised PEG-sulfonyl chloride (1) with but-3-yn-1-ol in dichloromethane in the presence of triethylamine gave rise to the corresponding PEGsupported but-3-yn-1-yl sulfonate (2), where the polymer species were easily obtained through precipitation by addition of propan-2-ol to the reaction mixture and then simple filtration. The linking reaction to the PEG support was monitored by the infrared absorption bands at 1371 cm -1 (S-O stretch of SO2C1), which was shifted to 1353 cm -1 (-SO2-O-), as well as by the appearance of a typical carbon-carbon triple bond absorption at 2122 cm -1 .…”

Facile and efficient sonochemical synthesis of 1,4-disubstituted 1,2,3-triazole derivatives catalyzed by CuI under mild conditions

“…Although organic azides are stable against most reaction conditions, compounds of low molecular weight or those containing several azides tend to be explosive and are difficult to handle [8], hence procedures involving generation of the azides in situ followed by azide alkyne cycloaddition have recently been reported [9][10][11][12][13][14].…”

Conventional and microwave assisted synthesis of 1,4-disubstituted 1,2,3-triazoles from Huisgen cycloaddition

“…Furthermore, Van der Eycken and coworkers used microwave-assisted click chemistry for the synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyst generated in situ by the comproportionation reaction of Cu(0) and Cu(II). 13 Fokin and co-workers 14 developed a method for the synthesis of 1,4-disubstituted 1,2,3-triazoles directly from a variety aryl and vinyl halides using a copper(I)-catalyzed proline-promoted reaction in a mixture of dimethylsulfoxide/water (9:1) or dimethylformamide/water (4:1) as the solvent, at 60 °C overnight.…”