Synthesis of amidrazones by the reaction between quinone arenalazines and ammonia

The reactions between quinone arenalazines or their chlorine derivatives and ammonia were investigated. It was shown that these reactions lead to the formation of amidrazones of 1,4-benzoquinone. The optimal preparative conditions for this reaction were determined. The reaction scheme involves the 1,8-addition of ammonia similar to the addition of mono-, dialkylamines and arylamines described earlier. The direct product of the addition instantly undergoes oxidation by air oxygen and cannot be separated in a pure form. The yields of the synthesized amidrazones depend on oxidation-reduction potential of initial quinone imine and grow with an increase in its magnitude. The structure of the obtained products was confirmed by the data of NMR spectroscopy and liquid chromatography– mass spectrometry. It was determined that amidrazones of 1,4-benzoquinone exist mainly in quinoid tautomeric form and the amount of other tautomers is negligible. The synthesized substances can be likely used as precursors of high range of heterocyclic compounds.