On the reaction of 3-nitro-1,2-phenylenediamine with ethyl acetoacetate. Condensed dihydrodiazepinones

Article abstract of DOI:10.1002/jhet.5570360430

Condensation of 3-nitro-1,2-phenylenediamine with ethyl acetoacetate in boiling xylene gave two isomeric 2,3-dihydro-4- methyl-9-nitro- and 2,5-dihydro-4-methyl-6-nitro-1H-1,5- benzodiazepin-2-ones, the 9-nitro derivative thermal rearrangement product N-isopropenyl-4-nitrobenzimidazolone and a non cyclic acetoacetamide derivative. At room temperature these reactants afforded 2,3-dihydro-2-ethoxycarbonyl-methyl-2-methyl- 4-nitrobenzimidazole.