Diazepines. Part V. 2,3-Dihydro-1H-1,4-diazepines

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Abstract
When equimolar mixtures of β-diketones and aliphatic 1,2-diamines are heated in acetic acid 2,3-dihydro-1H-1,4-diazepine derivatives are formed. If, however, 2 : 1 mixtures of these reactants are kept at room temperature, either in alcohols or without solvent, open-chain condensation products result. Glycinamide reacts with acetyl-acetone to give an azomethine rather than a diazepine. Perhydro-1,4-diazepine could not be dehydrogenated to a dihydrodiazepine. The 2,3-dihydro-1H-1,4-diazepinium cation is very stable, as evinced by the pK values of the diazepine and by its relative stability to permanganate oxidation.

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