(2S,5R)-2-Isopropyl-5-methylcyclohexanone Hydrazones

Abstract

Hydrazones were obtained in 76–78% yield via condensation of (2S,5R)-2-isopropyl-5-methylcyclohexanone with 4-R-phenoxyacetic acid hydrazides in the presence of a catalytic amount of glacial acetic acid. The structure of the target compounds has been established by FTIR-ATR, Raman, 1H-NMR and 13C-NMR spectral analysis and EI/FAB/ESI mass spectrometry. Thermal properties of hydrazones 3a–3e were elucidated by differential scanning calorimetry (DSC) and their purity by HPLC coupled to mass spectrometry. Synthesized compounds were found to exist as Z/E geometrical isomers about C=N bond and cis/trans amide conformers.