Synthesis of 3-arylazo-6-oxopyridazin-5-carbonitriles: A versatile precursor for condensed arylazopyridazin-6-ones

摘要

1-[2-Phenyl-1-diazenyl]-1-[2-phenylhydrazono] acetone or 1-[-2-(4-methylphenyl)-1-diazenyl]-1-[-2-(4-methylphenyl)hydrazono] -butan-2-one were produced via coupling the (E) 2-oxopropanal-1-phenyl-hydrazone or (E) 2-oxobutanal-1-(4-methylphenyl)hydrazone with aromatic diazonium salts. These formazanes condensed readily with ethyl cyanoacetate to yield 5-methyl-3-oxo-2-phenyl-6-phenlazo-2,3-dihydropyridazine-4-carbonitrile compound (9a), 5-ethyl-3-oxo-2-p-tolyl-6-p-tolylazo-2,3-dihydropyridazine-4-carbonitrile and/or 5-ethyl-3-oxo-2,6-di-p-tolyl-2,3-dihydropyridazine-4-carbonitrile that reacted with sulphur in presence of piperidine to yield the aminothienopyridazinones. The latter reacted with electron poor olefins and acetylenes to yield aminophthalazines. Compound (9a) reacted also with benzylidenemalononitrile to yield the arylazophthalazinone.