2-(ω-Chloroalkyl)tetramethoxycalixarenes are converted to 2-(ω-azidoalkyl)tetramethoxy- and cone-2-(ω-azidoalkyl) tetrapropoxycalixarenes, the former by substitution and the latter by demethylation to 2-(ω-chloroalkyl)tetrahydroxycalixarenes, which are O-propylated before substitution of azide for chloride. The azide-terminated calixarenes undergo Cu(I)-catalyzed 1,3-cycloaddition to terminal alkynes to give 1,4-disubstituted 1,2,3-triazoles, demonstrating the potential to couple calixarenes from a tether at the 2-position (methylene bridge) to substrates that bear a terminal alkyne group. The cone conformation of cone-2-(4- chlorobutyl)tetrapropoxycalixarene has been confirmed by X-ray diffraction.
|Number of pages||8|
|State||Published - Sep 16 2011|
Bibliographical noteFunding Information:
We thank Drs. Thomas A. Evans and Joseph J. Reczek for helpful comments. Support for this research by the Denison University and the Denison University Research Foundation is gratefully acknowledged.
- Click chemistry
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry