Acid-base properties of 2,3,4,5-tetrahydro-1H-naphtho[2,3-b]-1,4-diazepine-2,4,6, 11-tetraone

It is shown that 2,3,4,5-tetrahydro-1H-naphtho2,3-b]-1,4-diazepine-2,4,6,11-tetraone, which has acid properties, undergoes methylation to give an N,N-di-methyl derivative, whereas it gives products of substitution of the hydrogen atoms of the methylene group in its reactions with bromine and salicylaldehyde. Treatment of 2,3,4,5-tetrahydro-1H-naphtho2,3-b]-1,4-diazepine-2,4,6,11-tetrone with aqueous alkali or secondary aliphatic amines with heating is accompanied by opening of the diazepine ring to give hydrolysis (2-carboxyacetamido-3-hydroxy-1,4-naphthoquinones) or aminolysis (N-alkylaminomalonyl-2,3-diamino-1,4-naphthoquinones) products.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1132–1136, August, 1978.