Pd-catalyzed domino Heck cyclization/cross-coupling of indoles with β-chlorovinyl ketones: synthesis of furan-bearing indolo[2,1-α]isoquinolines with antifungal activity.

Herein, a palladium-catalyzed cross-coupling cascade cyclization of alkene-tethered indoles and (E)-β-chlorovinyl ketones, providing access to various furan-bearing indolo[2,1-α]isoquinolines, is reported. The reaction enables the rapid construction of one C-O bond and two C-C bonds to form bis-heterocycles. Furthermore, these furan-bearing indolo[2,1-α]isoquinolines exhibited certain antifungal activity in vitro. Notably, bis-heterocycles 3da (EC50 = 16.5014 μg mL-1) against Botryosphaeria dothidea and 3ar (EC50 = 18.2751 μg mL-1) against Rhizoctonia solani were identified to have good inhibitory effects.