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International Journal of Spectroscopy
Volume 2015 (2015), Article ID 609250, 9 pages
Research Article

Stereochemical Investigations of Diastereomeric N-[2-(Aryl)-5-methyl-4-oxo-1,3-thiazolidine-3-yl]-pyridine-3-carboxamides by Nuclear Magnetic Resonance Spectroscopy (1D and 2D)

1Department of Chemistry, Abant İzzet Baysal University, 14030 Bolu, Turkey
2Department of Pharmaceutical Chemistry, Istanbul University, 34116 Istanbul, Turkey

Received 13 October 2015; Revised 19 November 2015; Accepted 10 December 2015

Academic Editor: Craig J. Eckhardt

Copyright © 2015 Öznur Demir-Ordu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Some new N-[2-(aryl)-5-methyl-4-oxo-1,3-thiazolidine-3-yl]-pyridine-3-carboxamides were synthesized and their structures were investigated by IR, NMR (1H, 13C, and 2D), and mass spectra. The presence of C-2 and C-5 stereogenic centers on the thiazolidinone ring resulted in diastereoisomeric pairs. The configurations of two stereogenic centers were assigned based upon 1H NMR analysis of coupling constants and 2D nuclear overhauser enhancement spectroscopy (NOESY) experiment. Resolution of the diastereoisomers was performed by high performance liquid chromatography (HPLC) using a chiral stationary phase.