20080-08-4

Upstream product

• 959-23-9 4'-methoxychalcone 
• 117954-07-1 1-chloro-4-((1R*,2R*)-2-(p-tolyl)cyclopropyl)benzene 
• 88700-24-7 1-<(methylthio)thiocarbonylmethyl>pyridinium iodide 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 100-42-5 styrene 
• 38435-51-7 N-hydroxy-4-methoxy-benzenecarboximidoyl chloride 
• 102-92-1 cinnamoyl chloride 
• 100-66-3 methoxybenzene 
• 3717-21-3 p-methoxyl benzaldoxime 
• 123-11-5 4-methoxy-benzaldehyde 
• 1393358-28-5 4-methoxy-N-hydroxybenzimidoyl bromide 
• 15500-73-9 4-methoxybenzonitrile oxide 
• 5739-38-8 1-(4-methoxyphenyl)-3-phenylpropan-1-one 
• 20080-08-4 3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazole 

Downstream Products

• 3672-52-4 3-(4-methoxyphenyl)-5-phenylisoxazole 

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

Iron(iii)-catalyzed selective N-O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from: N -vinyl-α,β-unsaturated ketonitrones

An iron(iii)-catalyst controlled cyclization and selective N-O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(ii) acetate in combination with the prepared bidentate N-ligand was used.

Selectfluor-Bu4NI-Mediated C(sp3)-H Oxidation in Aqueous Media: Synthesis of Δ2-Isoxazolines from Oximes

The direct functionalization of an aliphatic C-H bond within a complex molecule through a free-radical pathway is a valuable tool in synthetic chemistry. Herein, we developed an efficient transition-metal-free approach to generate Δ2-isoxazolines from oximes by radical-mediated C(sp3)-H oxidation. Investigation of the mechanism suggested that in the presence of Selectfluor and Bu4NI, the homolysis of the in situ formed O-I bond generated an iminoxyl radical that facilitated subsequent 1,5-H transfer and C(sp3)-H oxidation. The title reaction involves Selectfluor-Bu4NI-mediated C-O bond formation in aqueous media under metal-free conditions. A variety of Δ2-isoxazolines are directly synthesized from oximes by remote intramolecular functionalization of C(sp3)-H bonds.

Metal-free DBU promoted regioselective synthesis of isoxazoles and isoxazolines

A new simple and efficient metal-free 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) promoted regioselective synthesis of 3,5-disubstituted isoxazoles and isoxazolines from aldoximes has been described. This method allows the reaction to proceed efficiently on aldoximes containing unprotected phenolic hydroxyl groups. Furthermore, with the use of higher equivalents of N-chlorosuccinimide, chloro-substituted isoxazoles and isoxazolines were obtained as the only products via tandem one-pot 1,3-dipolar cycloaddition followed by regioselective chlorination. This journal is

An environmentally benign synthesis of isoxazolines and isoxazoles mediated by potassium chloride in water

An effective and environmentally benign procedure for the synthesis of isoxazolines and isoxazoles has been developed by a cycloaddition of nitrile oxides with alkenes or alkynes in water. In this approach, potassium chloride is first oxidized into chlorine in water by the environmentally friendly oxidant Oxone, then aldoximes are oxidized into nitrile oxides by the in situ generated hypochlorous acid, finally a 1,3-dipolar cycloaddition between nitrile oxides and alkenes or alkynes occurs to provide the corresponding isoxazolines and isoxazoles in good yields.

Chiral differentiation of novel isoxazoline derivatives on clicked thioether and triazole bridged cyclodextrin chiral stationary phases

Isoxazoline derivatives have been disclosed in the art as having acaricidal and insecticidal activity and as potential precursors for the syntheses of natural products. This work first demonstrates the chiral resolution of isoxazoline derivatives that had not been studied before on native cyclodextrin (CD) chiral stationary phases (CSPs). Two structurally well-defined CSPs based on native CD were prepared via different click procedures and applied for the enantioseparation of isoxazolines. Most of the studied isoxazolines were found to be well resolved (Rs > 1.5) under reversed phase mode, especially 4NPh-OPr, which exhibits the best enantioselectivity and resolution (α = 2.22; Rs = 4.16). Optimal resolutions were achieved by evaluating the influences of mobile phase composition, substitution moieties and CSP linkages on the separation. This contribution verifies that excellent enantioseparation of isoxazolines can be accomplished on smartly designed native CD-CSP, which provides a facile and economic way to obtain enantiopure isoxazoline derivatives.

Hypervalent iodine-catalyzed cycloaddition of nitrile oxides to alkenes

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was fi

KF/Al2O3: Solid-supported reagent used in 1,3-dipolar cycloaddition reaction of nitrile oxide

The stereoselective synthesis of 2-isoxazolidine through 1,3-dipolar cycloaddition reaction of nitrile oxide, which is in situ generation from aldoxime in the presence of N-bromosuccinamide and solid-supported reagent KF/Al2O3 at room temperature, is reported. KF/Al2O3 is sufficiently basic such that it can replace organic bases such as Et 3N used in typical procedures and it catalyses the reaction to enhance the rate of the reaction.

Generation of nitrile oxides from oximes using t -BuOI and their cycloaddition

tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.

Oxidation of oximes to nitrile oxides with hypervalent iodine reagents

Iodobenzene diacetate in MeOH containing a catalytic amount of TFA efficiently oxidizes aldoximes to nitrile oxides. The latter may be trapped in situ with olefins in a bimolecular or an intramolecular mode. The new method enables the execution of tandem oxidative dearomatization of phenols/intramolecular nitrile oxide cycloaddition sequences leading to useful synthetic intermediates.