Background: Isoxazole derivatives are a class of heterocyclic compounds with significant pharmacological relevance, known for their antimicrobial, anticancer, and anti-inflammatory activities. These molecules are pivotal in medicinal chemistry due to their structural versatility and potential as drug candidates. This study explores a novel synthetic pathway to produce (3-(4-bromophenyl)-isoxazol-5-yl)-methyl acetate, aiming to expand the library of bioactive isoxazole derivatives for future pharmacological evaluations.
Methods: A three-step synthetic approach was employed to obtain the target compound. First, 2,4-dimethylbenzaldehyde was reacted with hydroxylamine hydrochloride in the presence of pyridine to form the corresponding oxime. This intermediate underwent a cyclization reaction with propargyl alcohol and sodium hypochlorite in dichloromethane, yielding the core isoxazole structure. Finally, esterification of the isoxazole derivative was performed using acetic acid and concentrated sulfuric acid to produce the desired compound. Structural characterization and purity analysis were conducted using FT-IR, ¹H NMR, and ¹³C NMR spectroscopy.
Results: The synthesis successfully yielded (3-(4-bromophenyl)-isoxazol-5-yl)-methyl acetate as a dark brown liquid with a 62% yield. FT-IR analysis revealed characteristic absorption bands at 1631 cm⁻¹ and 1716 cm⁻¹. The ¹H and ¹³C NMR spectra provided detailed confirmation of the compound’s structure, demonstrating the success of the synthetic route. Additional derivatives with fluorine and methoxy substituents were synthesized with yields of 60–72%.
Conclusions: This study outlines an efficient and reproducible synthesis of novel isoxazole derivatives with potential pharmaceutical applications. Future studies will focus on their biological activities and therapeutic potential.