Unexpected cyclization of dipyridyl-glycoluril in the presence of formaldehyde and strong acid: A new scaffold with a potential as an anion receptor

Saki N., Icli B., Cevheroglu O., Akkaya E. U.

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, vol.55, pp.219-222, 2006 (SCI-Expanded) identifier identifier


In an attempted synthesis of peripherally pyridine-substituted cucurbituril, an unexpected cyclized product was obtained. A careful NMR analysis followed by mass spectrometry and preliminary crystallographic analyses, helped us in resolving the structure. The structure has two quaternized pyridine functionalities and a groove suitable as a potential receptor site. In addition, just like the parent glycoluril structure, two remaining urea-derived nitrogens can be alkylated by alkyl halides. Thus, we believe this high yielding reaction may become an entry point to a new class of anion receptors.