Heterogeneously Catalyzed Synthesis of Imidazolones via Cycloisomerizations of Propargylic Ureas Using Ag and Au/Al SBA-15 Systems

The synthesis of imidazolones through the cycloisomerization of ureas, specifically propargylureas, has gained attention due to the large availability of starting materials. However, this type of synthesis normally requires the utilization of strong bases, such as NaOH, expensive homogeneous metal catalysts, such as Ag-, Au-, and Ru-based systems, or toxic and hazardous chemicals. Herein, a study of different synthetic routes for the preparation of imidazolones through the cycloisomerization of propargylic ureas under fast, mild, and environmentally friendly conditions with heterogeneous catalysis was undertaken. First, the synthesis were carried out under mild conditions using toluene and acetonitrile as solvents. Silver and gold nanoparticles supported on AlSBA-15 were used as heterogeneous catalysts. The catalysts were prepared by mechanochemical and microwave-assisted techniques. Sequentially, a range of solvents was replaced by the greener ethanol. Finally, all obtained results were combined in order to carry out the reaction using only water as solvent and promoter of the reaction. Aiming to expedite the procedure, the synthesis were carried out under conventional and microwave irradiation. © Copyright 2019 American Chemical Society.