Herein, a simple and regioselective synthesis of (2-hydroxyphenyl)(3-(trifluoromethyl/cyano/phosphonate)-1H-pyrazol-5-yl)methanones as pyrrolomycin analogues was reported. This reaction could proceed from 3-formylchromones and the corresponding diazo compounds by a silver-mediated one-pot cascade reaction under mild conditions with a broad substrate scope. Most of all, some products displayed potent antibacterial activities.