Unexpected Cyclization of Dipyridyl-glycoluril in the Presence of Formaldehyde and Strong Acid: A New Scaffold with a Potential as an Anion Receptor

  • Neslihan Saki
  • Burcak Icli
  • Orkun Cevheroglu
  • Engin U. Akkaya
Article

Abstract

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.

Keywords

cucurbituril cucurbituril derivatives glycolurils molecular scaffolds 

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Copyright information

© Springer 2005

Authors and Affiliations

  • Neslihan Saki
    • 1
  • Burcak Icli
    • 2
  • Orkun Cevheroglu
    • 2
  • Engin U. Akkaya
    • 2
  1. 1.Department of ChemistryKocaeli UniversityIzmitTurkey
  2. 2.Department of ChemistryMiddle East Technical UniversityAnkaraTurkey

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