Recherches en serie azabenzodiazepine—VIII : Hydrazinolyses d'azabenzodiazepinones et d'azabenzodiazepinethiones de type 1,5

The action of hydrazine on several azabenzo-1,5-diazepinones gives 3(5)-methyl-5(3) pyrazole and the corresponding heterocyclic diamines but the reaction with phenylhydrazine is more complicated and depends on the nature of the heterocycle attached to the seven member ring. In this case two reaction centres must be taken into account; the amide group and the carbon atom in the 6 position. According to experimental conditions hydrazinolysis of s-triazolotriazepinethiones and pyrazolodiazepinethiones give either 5-hydrazino s-triazolotriaze-pines or pyrazolylamino-triazole (or pyrazole) or 3-hydrazinopyrazoles and 3,4-diamino triazole. The mechanism suggested is addition of molecules of hydrazine in the 5 position followed by a transannular reaction to the 7 position.