Synthesis of some 3,5-diarylisoxazoline derivatives in ionic liquids media

Abstract

Biologically active isoxazoline derivatives were efficiently synthesized in excellent yields and in less reaction time using mild, effective and environmentally friendly butylmethylimidazolium bromide as solvent and catalyst. By use of this catalyst isoxazoline derivatives are produced via cyclization reaction of chalcone and hydroxylamine hydrochloride in ionic liquids media. The separation of the product was facile and the catalyst could be separated and recycled. Our method is very quick, safe and avoids the use of hazardous and expensive reagents and solvents

Anti‐corrosive property of bioinspired environmental benign imidazole and isoxazoline heterocyclics: A cumulative studies of experimental and DFT methods

“…The obtained isoxazoline derivatives (ISO1–ISO2a) was filtered, washed with water and recrystallized with ethanol. Schemes for the synthesis of heterocyclic compounds are presented as Scheme S1 and S2 whereas as FT‐IR spectra of the synthesized compounds are shown in Figure S1 . Molecular structure and their analytical data are given in Tables S1 and S2.…”

“…The extensive use of heterocyclic compounds as corrosion inhibitors is attributed to the fact that they can be easily synthesized from commercially available chemicals economically in high yield, and they provide high inhibition efficiency even in small concentration . Literature study reveals that several classes of heterocyclic compounds including imidazoline and isoxazoline derivatives are fascinating class of heterocyclic compounds which exhibit wide range of biological activity such as anti‐inflammatory, anti‐colvulsant, anti‐microbial, anti‐HIV, and so forth . Literature study reveals that a few imidazoline and isoxazoline derivatives have been evaluated as effective corrosion inhibitors for different alloys and metals in different corrosive environments …”

Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

“…Replacing the solvent by acetic acid, a series of 2-isoxazolines arises from the reaction of hydroxylamine hydrochloride in the presence of NaOAc with chalcone-based compounds bearing pyrrole [120], methylenebisthiazolidinone [121] and benzimidazole [122] moieties. Other modifications involve the use of pyridine [123][124][125] or triethanolamine [126] that act as both solvent and base. Refluxing bischalcones with hydroxylamine hydrochloride in pyridine afforded bisisoxazolines in high yields [127].…”

Understanding the molecular mechanism of the [3 + 2] cycloaddition reaction of benzonitrile oxide toward electron‐rich N‐vinylpyrrole: a DFT study

“…Several methods have been reported for the synthesis of isoxazoline derivatives. The synthetic routes for the preparation of isoxazoline derivatives are mainly the following: cyclization reaction of chalcones, [3 + 2] cycloaddition (32CA) reaction of oximes with alkenes, direct transformation of 3‐arylpropargyl hydroxylamines hydrochlorides, reaction of alkenes or alkynes with ketones, 32CA reactions of nitrile oxides with vinylic compounds, and cyclization of O‐propargylic hydroxylamines . Among the mentioned methods, 32CA reactions have proved to be the best and the general synthetic route …”