Nitriles in Organic Synthesis: Synthesis of new pyridazine,pyridine and pyrazolo[3,4-b]pyridine derivatives

The reaction of diethyl monoiminomalonate with benzoylacetonitrile affords the ethyl 3-amino-4-cyanopentanoate derivative 1 a . Compound 1 a condensed with salicylaldehyde to yield the coumarin 5 and coupled with arenediazonium salts to yield the arenehydrazones 6a – c . Compounds 6a , b could be converted into the aminopyridazinium carboxylate 8a , b on treatment with aqueous sodium hydroxide. The reaction of 6a – c with hydrazine and phenyl hydrazine is reported.