Synthesis of 1,2-diamines, 2-imidazolidinones and 2-imidazolidinethiones from α-haloimines

Article abstract of DOI:10.1055/s-1993-25989

α-Bromo- and α-chloroaldimines 1 are easily converted into α-azidoaldimines 2 which are reduced by lithium aluminum hydride to afford N-monoalkylated 1,2-diamines 3. In a similar way, aromatic α-bromoketimines 7 are transformed into the corresponding α-azidoketimines 8 and α-monoalkylated l,2-diamines 9. The 1,2-diamines, thus obtained, are converted into 2-imidazolidinones 4, 10 and 2-imidazolidinethiones 5, 11.