One step from nitro to oxime: a convenient preparation of unsaturated oximes by the reduction of the corresponding vinylnitro compounds

A series of novel unsaturated oximes were conveniently prepared from the corresponding vinylnitro compounds by reduction with SnCl2·2H2O. The structures of the oximes were characterized by 1H and 13C NMR, IR and HRMS, and X-ray crystallography analysis of 1-(6-chloro-pyridin-3-ylmethyl)-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime 2a reveals that, the hydroxyl group is arranged in a trans configuration. Some evidences from a brief investigation suggest that these oximes seem to be formed by reduction of the aci form of nitro aliphatic compounds.

Graphical abstractA series of novel unsaturated oximes were prepared from vinylnitro compounds by reduction and these oximes seem to be formed by reduction of the aci form of nitro compounds.Figure optionsDownload full-size imageDownload as PowerPoint slide