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Synthesis 2013; 45(16): 2245-2250
DOI: 10.1055/s-0033-1338490
DOI: 10.1055/s-0033-1338490
paper
‘Click’ [3+2]-Cycloaddition Approach to Novel Cookson’s Birdcage-Derived Thiacrown Ethers
Weitere Informationen
Publikationsverlauf
Received: 05. März 2013
Accepted after revision: 09. Mai 2013
Publikationsdatum:
18. Juni 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201316/lookinside/thumbnails/10.1055-s-0033-1338490-1.jpg)
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 compoundsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For the synthesis and biological activity of selected pentacycloundecane-derived compounds, see: