Abstract
This work focuses on the development of a new methodology for the regioselective functionalization of 4-azaindazole and 7-azaindazole N-oxide through oxidative alkenylation, specifically targeting the pyridine moiety. The study explores an unexplored area of regioselective oxidative alkenylation of 6,5-fused bicyclic compounds within the six-membered ring. The research also reports the isolation and characterization of hydroxylated products, involving C–O bond formation, which emerged as significant side products during this investigation. In this approach, N-oxide is proposed to play a dual role as a traceless directing group as well as a source of an oxygen atom. This catalytic method involves the simultaneous formation of new C–C and C–O bonds.