N-Bromosuccinamide (NBS)/Azoisobutyronitrile (AIBN) efficiently catalyzed pseudo four-component reaction is described, leading to the efficient regioselective synthesis of σ symmetric spiro heterobicyclic rings using aldehydes and urea in the presence of cyclic β-diester or β-diamides such as Meldrum’s acid or barbituric acid derivatives. The reaction proceeds in solvent-free conditions at 800 C.