Facile synthesis, crystal structure, Hirshfeld surface analysis, DFT calculations, IR and UV–visible spectra analyzes, ADMET and molecular docking studies of arylideneisoxazolone derivatives

• Published in: Journal of molecular structure Vol. 1317; p. 139005
• Main Authors: Boureghda, Chaima, Krid, Adel, Dems, Mohamed Abdesselem, Boutebdja, Mehdi, Boulcina, Raouf, Debache, Abdelmadjid
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 05.12.2024
• Subjects: Arylideneisoxazolone; Cristal structure; DFT; Molecular docking; Multicomponent reaction; Sulfamic acid; Arylideneisoxazolone; Multicomponent reaction; DFT; Sulfamic acid; Cristal structure; Molecular docking
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.139005

•A highly efficient method of the synthesis.•The use of an eco-friendly solvent.•Easy implementation of the reaction.•Purification of compounds without column chromatography.•In-depth theoretical study. Isoxazolone derivatives exhibit numerous biological and pharmacological activities. The search of new procedures for the synthesis of this class of heterocycles is still relevant. Thus we propose a new efficient method for the preparation of a series (4a-4j) of 3-methyl-4-arylidene-isoxazol-5(4H)-ones by the three-component reaction between aromatic aldehydes, ethyl acetoacetate and hydroxylamine hydrochloride, catalyzed by sulfamic acid as an inexpensive, commercially available and easy to handle catalyst. The expected molecules were obtained, in general, in good yields in relatively short reaction times and their structures were elucidated by 1H and 13C NMR and high resolution mass spectrometry for the new compounds. In addition, the structure of compound 4c was confirmed by X-ray diffraction and its Hirshfeld surface analyzed. The work is complemented by theoretical studies including DFT calculations, IR vibrations and UV–Vis electronic transitions analyzes and ADMET properties. In Silico physicochemical properties as well as molecular docking were also carried out.