Reactions of Diethyl [(3-Bromomethyl-2-Thienyl)-Methylene]Propanedioate with Hydrazines: Syntheses of Dihydropyridazines,Pyridazines and O-Dimethylaminomethylarenecarbonitriles

Facile syntheses of dihydropyridazines, pyridazines, and o-dimethylaminomethylarenecarbonitriles have been achieved by the retro-malonate addition reaction. Bromoalkylidenemalonates 1,7, and 10 were treated with hydrazine to give dihydropyridazines 4, 8, and 11 in quantitative yields. DDQ or air oxidation of 4, 8, and 11 gave pyridazines 5, 9, and 12, Alternatively, treatment of 1, 7, and 10 with 1,1-dimethylhydrazine afforded o-dimethylaminomethylarenecarbonitriles 6,13, and 14 in good yields.