Click [3+2]-cycloaddition approach to novel Cookson's birdcage-derived thiacrown ethers

Article abstract of DOI:10.1055/s-0033-1338490

The synthesis of novel Cookson's birdcage-annulated thiacrowns as well as noncage oligomers with an incorporated 1,2,3-triazole moiety are described. The title compounds were prepared applying a click alkyne-azide cycloaddition reaction in the final macrocyclization step. Using this methodology a series of oligomers containing oxygen, nitrogen, and sulfur were prepared. The effective cycloaddition process was carried out under nonaqueous conditions in the presence of a catalytic amount of copper(I) iodide and N,N- diisopropylethylamine; the yields of oligomers were moderate to good. Georg Thieme Verlag Stuttgart. New York.