As one of the privileged scaffolds, indolizine has been widely utilized as a core structure with various biological activities in small molecule drug discovery research. [3+3] Annulative functionalization strategies with 2-chloromethylindolizine were employed for facile construction of additional (hetero)cyclic ring(s) to furnish two novel indolizine-fused skeletons, 6H-chromeno[3,4-b]indolizine and pyrido[1,2-a]indole.