Copper-Catalyzed Synthesis of Pyrrolo[1,2- c ]quinazolines and Pyrrolo[2,1- a ]isoquinolines and Antiplasmodial Evaluation.

Reactions involving C(sp 3 )-H bonds of azaarenes have been widely studied in recent years as they allow direct functionalization of these N -heterocycles without the use of harsh reaction conditions. In this work, we describe the C(sp 3 )-H functionalization of 4-methylquinazolines and 1-benzylisoquinolines, employing α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate. Under the optimized condition, 21 pyrrolo[1,2- c ]quinazolines, as well as an imidazo[1,2- c ]quinazoline and 4 pyrrolo[2,1- a ]isoquinolines, were obtained in moderate to good yields. Furthermore, the biological activity of the pyrrolo[1,2- c ]quinazolines was evaluated against Plasmodium falciparum , and promising results were obtained.