Synthesis and NMR characterization of tethered quinolines

ORGN 544

Adam J. Beck, ajb5760@uncw.edu, Department of Chemistry and Biochemistry, University of North Carolina - Wilmington, 601 S. College Rd., Wilmington, NC 28403, Pamela J. Seaton, seatonp@uncw.edu, Department of Chemistry and Biochemistry, University of North Carolina, Wilmington, NC 28403, and Abhijit Mitra, abhijit.mitra@manhattan.edu, Department of Chemistry and Biochemistry, Manhattan College/College of Mount St. Vincent, Riverdale, NY 10471.
Quinolines are an important group of bioactive heterocyclic compounds found in many pharmaceuticals. Recent studies have shown quinolines to demonstrate unusual concentration dependent chemical shift changes in 1H-NMR spectra. It is proposed that these changes are due to π-π interactions between two or more quinoline molecules. Several quinoline monomer and dimer analogs have been synthesized to further study their concentration-dependent 1H-NMR behavior. The effect of attachment and functional group on the quinoline ring, using C3, C6 and C10 tethers, were evaluated through 1H-NMR studies. The concentration dependent chemical shifts of the 6-substituted quinoline dimer (1) were smaller than those of the equivalent monomer (2). However, the 8-substituted dimers had similar chemical shifts compared to the monomers. This data is consistent with the 6-substituted dimers being able to stack intramolecularly in an anti-parallel conformation (1).

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006