A facile and dependable synthetic route for 5-amino-4-sulfonyl pyrazoles, which are substantially important in pharmaceuticals, is highly desirable. This work presents a novel cascade reaction for their efficient synthesis. The approach utilizes silver as a catalyst for C(sp2)-H sulfonylation of readily available starting materials 1,2-diaza-1,3-dienes with sulfinate salts, followed by intramolecular cascade cyclization annulation to afford the desired 5-amino-4-sulfonyl pyrazoles in good to excellent yields under mild conditions.