Unexpected Cyclization of Dipyridyl-glycoluril in the Presence of Formaldehyde and Strong Acid: A New Scaffold with a Potential as an Anion Receptor
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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.
Keywordscucurbituril cucurbituril derivatives glycolurils molecular scaffolds
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