13C NMR spectral assignment of 1,4-diarylpiperazinones

The piperazinone derivatives have potential application in the pharmaceutical, polymer and textile fields. The present work describes the preparation of a series of new 1,4-diaryisubstituted-2-piperazinones by condensation of substituted N,N'-bis-(2-hydroxyphenyl)-ethylenediamines with glyoxal and the complete C-13 NMR spectral assignment accomplished using APT, HMQC and HMBC techniques. Substituent chemical-shift effects (SCS) were calculated, which showed different values for the lactarn- and aminesubstituted aromatic rings. The results show that predictions based on SCS effects are not simple for these molecules due to electronic and steric effects. Moreover, in the case of the ortho-substituted derivative 2 g, the NMR spectra reveal a dynamic behavior related to restricted rotation of the phenyl groups (atropisomerism). Copyright (c) 2005 John Wiley & Sons, Ltd.