EFFICIENT SYNTHESIS OF N-SUBSTITUTED LACTAMS FROM (N-ARYLSULFONYLOXY)AMINES AND CYCLIC KETONES

Article abstract of DOI:10.1016/S0040-4039(01)80691-2

A new method is reported for the direct preparation of N-substituted lactams from cycloalkanones.N-(p-nitrobenzenesulfonoxyl) methylamine 1a (CH3NH-OSO2C6H4NO2) was reacted with a series of cycloalkanones to give good yields of N-methyl lactams.An addition-rearrangement pathway accounts for the ring-expanded lactam products.A series of N-alkyl-N-arylsulfonoxyl amines were generated in situ and reacted with cyclobutanone to give N-alkyl pyrrolidinones in high yields.