37613-34-6

Upstream product

• 459-23-4 4-fluorobenzaldoxime 
• 536-74-3 phenylacetylene 
• 459-57-4 4-fluorobenzaldehyde 
• 39833-45-9 3-(4-fluorophenyl)-1-phenylprop-2-yn-1-one 
• 403-43-0 4-fluorobenzoyl chloride 
• 82677-84-7 1-(4-fluorophenyl)-3-phenylprop-2-yn-1-one 
• 98-88-4 benzoyl chloride 
• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 399-10-0 4'-fluorochalcone 

Downstream Products

• 80223-02-5 3-(4-Fluoro-phenyl)-2-methyl-5-phenyl-isoxazol-2-ium; iodide 

Relevant academic research and scientific papers

TEMPO-Mediated Selective Synthesis of Isoxazolines, 5-Hydroxy-2-isoxazolines, and Isoxazoles via Aliphatic δ-C(sp3)-H Bond Oxidation of Oximes

Selective synthesis of three different bioactive heterocycles; isoxazolines, 5-hydroxy-2-isoxazolines and isoxazoles from the same starting material using TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) as a radical initiator is reported. Selectivity was achi

Green preparation method of isoxazole compound participating in water-soluble vitamin E

The invention provides a green synthesis method of an isoxazole compound represented by the formula (III), wherein the aldehyde oxime compound represented by the formula (I) is a substrate and is in an aqueous solution of a surfactant with a mass concentration 1 wt % - 5 wt % in N - chlorosuccinimide. The alkyne compound represented by the formula (II) is reacted 6 - 16h at room temperature under the common action of the basic substance, and the resulting reaction solution is post-treated to obtain the isoxazole compound represented by the formula (III). Water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized.

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.

Catalyst control in positional-selective C-H alkenylation of isoxazoles and a ruthenium-mediated assembly of trisubstituted pyrroles

High levels of catalyst control are demonstrated in determining the positional selectivity in C-H alkenylation of isoxazoles. A cationic rhodium-mediated, strong-directing group promotes C(sp2)-H activation at the proximal aryl ring whereas, the palladium-mediated electrophilic metallation leads to the C(sp2)-H activation at the distal position of the directing group. Synthetic elaboration of this C-H alkenylation product via ruthenium and copper co-catalysis leads to an efficient method for the assembly of densely substituted pyrroles.

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.

Aerobic oxidative synthesis of 3,5-disubstituted isoxazoles directly from α,β-unsaturated ketones

Using an efficient aerobic oxidative method, the synthesis of ten 3,5-disubstituted isoxazoles by treatment of α,β-unsaturated ketones with hydroxylamine and NaOH at room temperature has been achieved.

A direct access to isoxazoles from ynones using trimethylsilyl azide as amino surrogate under metal/catalyst free conditions

A general method for isoxazoles from readily available ynones using trimethylsilyl azide as an amino surrogate, likely via an unprecedented hydroazidation of the alkyne and denitrogenative cyclization, is demonstrated. The method neither required any cata

Synergistic effect of dual-frequency ultrasound irradiation in the one-pot synthesis of 3,5-disubstituted isoxazoles

Herein is reported a one-pot three-step process for the regioselective synthesis of 3,5-disubstituted isoxazoles based on copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides (from the corresponding aldehydes) and alkynes, u

Facile Synthesis of Fluorine containing 1,3,5-triarylpyrazoles and 3,5-Diarylisoxazoles

Fluorine containing 1,3-diarylchalchones on condensation with pentafluorophenylhydrazine in absolute ethanol, afforded the corresponding 1,3,5-triarylpyrazoles and with hydroxyl amine hydrochloride in pyridine yielded 3,5-diarylisoxazoles.Fluorinated chalchones were synthesised by condensation of the appropriate acetophenones and aromatic aldehydes in aqueous ethanolic sodium hydroxide solution.All the compounds were characterised by their analytical and ir, 1H nmr, 19F nmr and mass spectral data.Mass fragmentation patterns of these compounds have also been discussed.