Preparation of an oxetan-phenyltetrahydropyridazine-3,6-dione derivative using some chemistry tools

The aim of this study was to synthesize a new oxetan-phenyltetrahydropyridazine-3,6-dione derivative (compound 6) using different techniques. The first method was achieved by the preparation of a phenylhydrazine derivative (2) using three-components system (3,17-aldol-estradiol, phenylhydrazine, 5-hexyn-3-ol) in the presence of Copper(II). Then, 2 was reacted with tert-butyldimethylsilyl chloride to form the compound 3 (trimethylbutan-silyloxy-steroid-hydrazine). Following, a pyridazine derivative (4) was prepared by the reaction of 3 with succinic acid using boric as catalyst. The compound 4 was reacted with hydrofluoric acid to form the tetrahydropyridazine-3,6-dione (5). Finally, the preparation of 6 was carried out by the reaction of 5 with CopperII. Spectroscopy analyses NMR was used to confirm the chemical structure of compounds. In conclusion, a facile method to synthesize an oxetan-phenyltetrahydropyridazine-3,6-dione is reported.