Tandem one-pot five-component reaction involving saccharin, propargyl bromide, aldehyde, hydroxylamine hydrochloride, and non-conjugated primary amine has been explored for a rapid and an efficient synthesis of isoxazole-secondary sulfonamides. This novel multicomponent reaction involves one pot Npropargylation of saccharin, oximation, and 1,3-dipolar cycloaddition, followed by an intermolecular ring-opening reaction by N-nucleophilic amine. This transformation is catalyzed by CaCl 2 /K 2 CO 3 and activated under ultrasonic cavitation. The CaCl 2 salt is reported for the first time as a new precatalyst and a chlorine source. We showed that ultrasound, using sonotrode, significantly improved the reaction compared to ultrasonic bath and magnetic stirring. The isoxazole-secondary sulfonamides 6 a-r were obtained in good to excellent yields (75-96 %) and withing shorter reaction times (13-17 min). All the synthesized compounds were fully characterized by IR, MS-ESI, 1 H NMR, 13 C NMR spectroscopy, X-ray crystallography and HPLC analysis.
In this work, a novel compound N-(3-(4-methoxyphenyl)isoxazolin-5-yl)methylsaccharin has been synthesized. The molecular structure of the compound was determined using various spectroscopic techniques and confirmed by a single-crystal X-ray diffraction analysis. In the single crystal, C–H…O hydrogen bonds between neighboring molecules form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H…H (35.7%), H…O/O…H (33.7%), and H…C/C…H (13%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 4.9266 eV.
In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition using sodium dichloroisocyanurate (SDIC) as an eco-friendly and inexpensive oxidizing agent under ultrasound cavitation in water as a green solvent. The desired compounds 4a–c were obtained in high to excellent yields of 75–90%.
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