A Selectfluor mediated regioselective π‐extended [3+1+1] annulation using imidazopyridines, acetophenones and DMF as carbon source has been realized. The current route compared to traditional π‐extended annulation reaction utilizes commercially available acetophenones as a cyclic partner and offers three C−C bond formations. This reaction displayed good functional group tolerance wherein DMF served as a carbon synthon. Five‐membered bridged chroman‐4‐one derivative of imidazopyridine has been achieved with 2‐hydroxy acetophenone, wherein DMF acted as a dual carbon synthon and offered four C−C and one C−O bond formation in one‐pot. [ABSTRACT FROM AUTHOR]