Ultrasound-assisted synthesis of aromatic 1,2-diketones from oximinoketones under neutral conditions in aqueous media

We report a convenient, neutral, and facile methodology for the synthesis of aromatic 1,2-diketones from the corresponding oximinoketones in the presence of I2/SDS/water system under ultrasound-assisted conditions. Furthermore, a series of compounds were synthesized and characterized by melting point, IR, NMR, MS, and elemental analysis. Utilization of easy reaction conditions, very high to excellent yields, and short reaction times makes this manipulation potentially very useful.

► A facile methodology for the synthesis of aromatic 1,2-diketones from the oximinoketones. ► Ultrasonic irradiation accelerates these transformations. ► The reaction proceeded efficiently with various aryl groups and no alkyl 1,2-diketones were obtained from reactions with alkyl groups. ► Electronic effects and the nature of substituents on the aromatic ring did show effects in terms of reaction times. ► Iodine is an efficient catalyst in the presence of SDS for the cleavage of the CN bond.