20822-00-8

Upstream product

• 873-67-6 benzonitrile oxide 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 14525-88-3 1-(4-bromophenyl)-2-phenylcyclopropane 
• 96-09-3 styrene oxide 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 932-90-1 Benzaldoxime 
• 25327-36-0 (Z)-2-(hydroxyimino)-2-phenylacetic acid 
• 156605-56-0 1-phenylethan-1-one O-pivaloyl oxime 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 53573-22-1 5-(p-bromophenyl)-3-phenyl-2-isoxazole 

Relevant academic research and scientific papers

Heteroannulation of Alkenes with Enynyl Benziodoxolones and Silver Nitrite Involving CC bond Oxidative Cleavage: Entry to 3-Aryl-?2-isoxazolines

A copper-catalyzed [2 + 2 + 1] heteroannulation of alkenes with enynyl benziodoxolones and AgNO2 involving oxidative cleavage of the CC bond promoted by cooperative Zn(OTf)2, KOAc, and 4 ? MS for producing 3-aryl δ2-isoxazolines is reported. Mechanistic s

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.

Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization

A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C-N and C-O bonds and intermolecular C-C bonds from aromatic alkenes or alkynes and N -hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C-H and C-C bonds/construction of C-O bonds/elimination of SO 2 /C-N bond formation is achieved in sequence in the reaction system.

Base-Promoted [3+2]-Annulation of Oxime Esters and Aldehydes for Rapid Isoxazoline Formation

A base-promoted [3+2]-annulation of ketoxime esters and aldehydes is disclosed for the facile and rapid synthesis of 3,5-disubstituted and 3,4,5-trisubstituted isoxazolines. The key to our success is the pivalate leaving group of the oxime substrates, combined with cesium carbonate as promoter. This chemistry allows the assembly of a vast array of isoxazoline derivatives under simple base conditions in a method complementary to the classic isoxazoline formation via [3+2]-dipolar cycloaddition of nitrile oxides and olefins. It also represents a new reaction pattern involving electrophilic amination/N–O bond substitution. (Figure presented.).

3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof

The invention relates to 3,4,5-trisubstituted-4,5-dihydroisoxazole, a derivative and a synthetic method and an application thereof. The invention mainly relates to a synthetic method of an isoxazoline compound. With adoption of a technical scheme that an aldehyde compound and oxime ester are converted into isoxazoline and the derivative thereof by taking an organic solvent as a solvent under the action of alkali without using a catalyst, the synthetic method solves the problem that an existing synthetic method of the isoxazoline compound is complicated in synthetic step, is accomplished by adopting multiple steps, and also needs a metal catalyst, a chemically equivalent metal oxidant or a peroxide. The atom economy is kept to the extreme extent; the isoxazoline compound has a stable molecular structure and an excellent chemical property, and molecular slices and compound segments contain rich contents with biological activity and pharmacological activity. The isoxazoline compound also has the characteristics of being simple in reaction system, mild in reaction condition, relatively less in reaction equipment, simple in experimental operation, wide in source of materials, high in yield, easy for expansion of user and application, relatively high in utilization value of product and expectable in market commercial prospect.

Visible-light-mediated generation of nitrile oxides for the photoredox synthesis of isoxazolines and isoxazoles

Visible-light photoredox catalysis enables the synthesis of biologically relevant isoxazolines and isoxazoles from hydroxyimino acids. The process shows broad functional group compatibility and mechanistic and computational studies support a visible-light-mediated generation of nitrile oxides by two sequential oxidative single electron transfer processes.

One-pot synthesis of isoxazolines from aldehydes catalyzed by iodobenzene

A convenient one-pot, three-step procedure for the synthesis of isoxazolines starting from aldehydes has been developed involving catalytic cycloaddition between nitrile oxides and alkenes, in which iodobenzene is used as the catalyst for the in situ generation of a hypervalent iodine intermediate. In this approach, the aldehydes are first transformed with hydroxylamine sulfate into aldoximes, which are then oxidized to nitrile oxides by the in situ generated hypervalent iodine intermediate; finally, a 1,3-dipolar cycloaddition between the nitrile oxides and alkenes occurs to provide the isoxazolines in moderate to good yields.

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.

Hypoiodite mediated synthesis of isoxazolines from aldoximes and alkenes using catalytic KI and Oxone as the terminal oxidant

Isoxazolines can be efficiently synthesized in good yields via a hypoiodite mediated catalytic oxidative cyclization of aldoximes and alkenes. This reaction involves active iodine species generated in situ from catalytic amounts of KI and Oxone.

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.