ENANTIOMERS OF STERICALLY HINDERED N-ARYL-4-PYRIDONES. CHROMATOGRAPHIC ENRICHMENT AND THERMAL INTERCONVERSION

Article abstract of DOI:10.1016/S0040-4020(01)83492-X

N-aryl-4-pyridones 1-6 were synthesized by condensation of the corresponding 4-pyrone with anilines.The enrichment of the enantiomers was achieved by liquid chromatography on triacetylcellulose, enantiomeric purities of (+)-1 and (+)-2 being measured by 1H NMR in the presence of an optically active auxiliary.Barriers to partial rotation about the C-N bond in 1-4 were determined and compared with corresponding biphenyls.