An efficient method has been developed for the cascade synthesis of azo[1,2-a]indolones from azoles and 2-fluoroaldehydes based on an iron-catalyzed SNAr and a direct acylation reaction. A number of azo[1,2-a]indolones containing different azole rings and substituents were obtained in good yields. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.