Environmentally Benign Synthesis of Quinoline–Spiroquinazolinones by Iron-Catalyzed Dehydrogenative [4 + 2] Cycloaddition of Secondary/Tertiary Anilines and 4-Methylene-quinazolinones

Abstract

We report an efficient iron-catalyzed cross-dehydrogenative coupling [4 + 2] annulation of secondary/tertiary anilines with quinazolinones to generate quinoline-spiroquinzolinones. The reaction proceeds smoothly with a relatively broad variety of functional groups, a cheap transition metal catalyst (FeCl3), and environmentally friendly oxidant (H2O2/O2) under mild reaction conditions. Creatively, N-methylanilines are employed for the first time for the cycloaddition as both methyl and methylene sources attached to the N atom of tetrahydroquinolines.