An improved method for the generation of imines and enamides. Application to the synthesis of 3-arylisoquinoline derivatives

Article abstract of DOI:10.1016/S0040-4020(01)85079-1

The one-pot preparation of hindered 1,2-diarylethylamines 3 and 4 and ethylenenamides 5 is achieved via sodium cyanoborohydride reduction and acylation of the deoxybenzoin imines 2, respectively. A new methodology for the synthesis of 3-arylisoquinolinium salts by the Bischler-Napieralski reaction of 1,2-diarylethylenenamides and their transformation into 12-methyl substituted benzo[c]phenanthridines has been developed.