ABSTRACT: Coupling of 4-antipyrinyldiazonium chloride (2) with N,N"-dimethylhydrazine and hydrazine hydrate afforded 1,6-di(4-antipyrinyl)hexaaza-1,5-dienes. Whereas, coupling of 2 with the appropriate hydrazone or hydrazide gave tetraazenes or 1,4-pentaazadienes, depending on the molar ratio of the reactants. Diazotization of isonicotinic acid hydrazide followed by coupling with antipyrine and 4-aminoantipyrine was investigated.