3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles

Abstract

In this study, 3-benzoylisoxazolines were synthesized by reacting alkenes with various α-nitroketones using chloramine-T as the base. The scope of α-nitroketones and alkenes is extensive, including different alkenes and alkynes to form various isoxazolines and isoxazoles. The use of chloramine-T, as the low-cost, easily handled, moderate base for 1,3-dipolar cycloaddition is attractive.

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

“…In the key stage, the cycloaddition of acid-introtautomer of nitro compounds takes place. The resulting tetrahydroisoxazole is then transformed into isooxazoline [ 305 ]. Many similar syntheses (Michael Additions versus Cycloaddition Condensations) involving nitro compounds leading to 2–isoxazolines were previously published by Trogu et al [ 306 ].…”

Novel Synthesis of Dihydroisoxazoles by p-TsOH-Participated 1,3-Dipolar Cycloaddition of Dipolarophiles withα-Nitroketones

“…In the previous study, we first used the alkaline catalyst chloramine-T to catalyze the reaction of α-nitroketone and alkene to synthesize isoxazoline with a yield of 77% [ 42 ]. In the present work, we report a novel synthesis of dihydroisoxazoles by p -TsOH (anhydrous)-participated 1,3-dipolar cycloaddition of isoxazoline with α -nitroketones.…”

“…The following supporting information can be downloaded at: , The Supplementary Materials contain experimental protocols, analytical data for products and NMR spectra [ 29 , 42 , 46 , 48 , 49 , 50 ].…”