Tunable Sulfenylnitrenes Enable Scaffold Hopping of Furans into N-Heterocycles

Abstract

Furans are readily available heteroaromatic scaffolds valued for their structural rigidity, tunable electronic properties, and functional versatility. Transforming furans into nitrogen-containing heterocycles is an efficient strategy for expanding molecular diversity and enhancing chemical and biological properties. N-heterocycles such as pyrimidines, pyrroles, and pyridazines often exhibit improved stability, enhanced hydrogen-bonding capacity, and favorable pharmacokinetic profiles. Herein, we report a scaffold-hopping strategy that converts furans into N-heterocycles using tunable sulfenylnitrenes. Mechanistic investigations, including isotopic labeling experiments supported by DFT calculations, reveal a unique reaction pathway.