Reactivity of 1‐Aryl‐3‐Nitro‐ and 1‐Aryl‐3‐Bromo‐3‐Nitropropenones With Semicarbazides and Benzohydrazide: Convenient Synthesis of Monohydrazones of α‐Diketones

ABSTRACT Conjugated nitroalkenes, particularly 1‐aryl‐3‐nitroprop‐2‐en‐1‐ones, represent a valuable class of electrophilic substrates due to the presence of electron‐withdrawing groups that enable selective nucleophilic attacks. This study explores the reactivity of these nitropropenones and their brominated analogs with benzohydrazide, phenylsemicarbazide, and semicarbazide. The reactions predominantly proceed via aza‐Michael addition, yielding adducts that can be further transformed through elimination of HNO 2 or HBr to monohydrazones of α‐diketones with good to excellent yields. Structural studies, including NMR and x‐ray crystallography, revealed the E‐s‐trans configurations of the synthesized compounds. Importantly, in silico PASS analysis predicts high potential biological activities for the synthesized compounds, notably as inhibitors of various enzymes. These findings highlight the synthetic accessibility and promising pharmacological profile of nitroalkene‐derived hydrazone compounds, encouraging their further exploration for therapeutic applications.