Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

The cationic Ru-H complex [(C6H6)(PCy3)(CO)-RuH]+BF4- (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2'-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.

Automated summary

A highly effective catalyst, the cationic Ru-H complex, was found to facilitate the deaminative coupling reaction of 2'-hydroxyaryl ketones with simple amines to form flavanone products. Similarly, the reaction of 2-aminobenzamides with branched amines yielded quinazolinone products. This catalytic method efficiently installs useful core structures without the need for reactive reagents.