Generation of aryl(2-lithiophenyl)methanone O-methyl oximes and their use for the synthesis of N-(3-alkyl-1-aryl- or 1,3-diaryl-1H-isoindol-1-yl)-O- methylhydroxylamines via the reaction with nitriles

Article abstract of DOI:10.1002/hlca.201400067

An efficient two-step procedure for the preparation of a new type of 1H-isoindoles, i.e., N-(3-alkyl-1-aryl- or 1,3-diaryl-1H-isoindol-1-yl)-O- methylhydroxylamines 5, from readily available aryl(2-bromophenyl)methanones 1 has been developed. Aryl(2-bromophenyl)methanone O-methyloximes 2, derived from the corresponding ketones, were treated with BuLi in Et₂O at 0° to generate novel lithium compounds, aryl(2-lithiophenyl)methanone O-methyloximes 3, which were allowed to react with nitriles to give the desired products 5 in moderate-to-fair yields. Copyright