Direct Assembly of Vinyl Fluorinated Isoquinolines Via Rh(III)-Catalyzed [4 + 2] Annulation

Abstract

Efficacious access to build fluorovinyl isoquinolines has been disclosed via Rh(III)-catalyzed C–H functionalization between oxadiazoles and difluoromethylene alkynes with excellent chemoselectivity and regioselectivity. This protocol presents a practical method to install the fluorovinyl motif in the expected position of isoquinoline frameworks with wide functional group compatibility.

Ruthenium(II)-Catalyzed Annulation of Oximes with Maleimides: Synthesis of Pyrrolo[3,4-c]isoquinoline-1,3-diones

“…Isoquinolines as one of the most abundant alkaloid scaffolds have a vital role in natural and biological active products. − Some of the privileged isoquinolines, such as moxaverine, dimoxyline, and pulcheotine, are known as effective drugs in medicinal chemistry. − Among the well-known pyrrolo-fused heterocyclic compounds with pharmacological and biological activities, pyrroloisoquinolines and pyrrolopyridines hold a privileged position. − Potent drugs, including PNKP inhibitors, GSK-3β inhibitors, and DPP4 inhibitors, which exhibit effective functions against cancer cells, Alzheimer’s disease, and diabetes, respectively, incorporate the pyrroloisoquinoline and pyrrolopyridine cores into their structural frameworks (Scheme A). By considering the indispensable role of isoquinolines in diverse pharmaceuticals, natural products, and druglike scaffolds, finding efficient routes to provide this valuable structure is highly demanded. − …”