‘Click’ [3+2]-Cycloaddition Approach to Novel Cookson’s Birdcage-Derived Thiacrown Ethers

Abstract

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.

Key words

macrocycles - thiacrown ethers - click chemistry - 1,3-dipolar cycloaddition - cage compounds

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