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)

Abstract

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.