Unexpected Cyclization of Dipyridyl-glycoluril in the Presence of Formaldehyde and Strong Acid: A New Scaffold with a Potential as an Anion Receptor
- 142 Downloads
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
Unable to display preview. Download preview PDF.
We gratefully acknowledge support from Kocaeli University BAP Funds and METU University Research Funds.
- 5.Mock W.L., (1995). Top. Curr. Chem. 175: 1Google Scholar
- 10.D. Tuncel and J.H.G. Steinke: Chem. Commun. 253 (2001)Google Scholar
- 13.W.L. Lock: in F. Vögtle (ed.), Comprehensive Supramolecular Chemistry, Vol. 2, Elsevier Press, New York (1996), p. 477Google Scholar
- 22.J.N.H. Reek, A. Kros, and R.J. Nolte: Chem. Commun. 245 (1996)Google Scholar