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