10.1016/j.tet.2008.09.043
This research presents an efficient method for the synthesis of 5-amino?avones, an important class of natural compounds within the ?avonoid group known for their various biological activities such as antiestrogenic, antitumor, antiallergic, and antiin?ammatory properties. The authors developed a microwave-assisted SNAr (Nucleophilic Aromatic Substitution) reaction to access 5-amino?avones, which allows for the introduction of an amino group directly onto the ?avone nucleus, a less commonly reported approach. The process involves the protection of diosmetin with benzyl bromide, followed by tri?ation and amination using various amines. The study concluded that this methodology yields good results with primary and secondary non-aromatic amines and even moderate yields with anilines, without the need for palladium catalysts or hard bases. Key chemicals used in the process include diosmetin, benzyl bromide, N-phenylbistri?imide (PhNTf2), and a range of amines such as benzylamine and its derivatives, as well as primary alkylamines and cycloalkylamines. The final step involved the removal of protective benzyl groups through catalytic hydrogenation to yield the final 5-amino?avone compounds.