Metal-free tandem Beckmann-electrophilic aromatic substitution cascade affording diaryl imines, ketones, amines, and quinazolines

Article abstract of DOI:10.1016/j.tetlet.2015.07.095

A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N-phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann-Ritter-EAS cascade.