Synthesis of 4-(4-hydrazinylphenoxy)phthalonitrile and phthalonitriles on its basis containing N-heterocycles

Abstract

The synthesis of the novel 4-(4-hydrazinylphenoxy)phthalonitrile was carried out for the first time by nucleophilic aromatic displacement of nitro group in 4-nitrophthalonitrile to aminophenoxy fragment with following diazotization of amino group and reduction of diazo intermediate. The novel phthalonitriles containing substituted pyrazole or pyrazolone fragments were obtained by reaction of 4-(4-hydrazinylphenoxy)phthalonitrile with different 1,3-dicarbonyl compounds. The structures of the compounds obtained were characterized by IR and 1 H NMR spectroscopy.