Diazepines. Part XII. 6-Nitro- and 6-amino-2,3-dihydro-1H-1,4-diazepinium salts

Abstract

2,3-Dihydro-1H-1,4-diazepinium salts (I) are nitrated at the 6-position by nitric acid–sulphuric acid mixtures or by nitric acid alone, at room or lower temperature. The 6-nitro-derivatives can be reduced to 6-aminodihydrodiazepines. The latter condense readily with aromatic aldehydes to form stable anils, and may be converted into diazonium salts. A 6-chlorodihydrodiazepinium salt was obtained from a 6-diazonium salts by means of a Sandmeyer reaction. NN′-Diphenyl-2,3-dihydro-1H-1,4-diazepinium salts are nitrated in both the benzene and the dihydrodiazepinium rings.