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)


DEMİR ORDU Ö., Demir-Dundar H., Ozkirimli S.

INTERNATIONAL JOURNAL OF SPECTROSCOPY, 2015 (ESCI İndekslerine Giren Dergi) identifier

  • Cilt numarası:
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1155/2015/609250
  • Dergi Adı: INTERNATIONAL JOURNAL OF SPECTROSCOPY

Özet

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(H-1, C-13, 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 H-1 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.