20821-97-0

Upstream product

• 637-69-4 4-Methoxystyrene 
• 873-67-6 benzonitrile oxide 
• 959-33-1 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
• 117954-06-0 1-methoxy-4-(2-phenylcyclopropyl)benzene 
• 22252-15-9 trans-4-methoxychalcone 
• 117954-07-1 1-chloro-4-((1R*,2R*)-2-(p-tolyl)cyclopropyl)benzene 
• 34221-26-6 trans-1-(4-methoxyphenyl)-2-phenylcyclopropane 
• 25327-36-0 (Z)-2-(hydroxyimino)-2-phenylacetic acid 
• 1669-49-4 3-(4-methoxyphenyl)-1-phenylpropan-1-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 98-86-2 acetophenone 
• 96-09-3 styrene oxide 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 3672-51-3 5-(4-methoxyphenyl)-3-phenylisoxazole 
• 66692-97-5 5-(4-methoxy-phenyl)-4-nitro-3-phenyl-isoxazole 

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

Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate

Abstract: The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF4 were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.

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.

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.

Synthesis of some 3,5-diaryl-2-isoxazoline derivatives in ionic liquids media

Biologically active isoxazoline derivatives were efficiently synthesized in excellent yields and in smaller reaction times using mild, effective and environmentally friendly butylmethylimidazolium bromide as the solvent and catalyst. By use of this cataly

Nitrosonium hexachlorostannate: Synthesis, crystal structure, and nitrosating activity in the reactions with arylcyclopropanes

Nitrosonium hexachlorostannate (NO)2[SnCl6] was synthesized by the reaction of NOCl and SnCl4 in CH 2Cl2. According to the single-crystal X-ray diffraction analysis data, the structure of (NO)2[SnCl6] consists of cations NO+ and octahedral anions [SnCl6]2- arranged as ions in antifluorite. Isoxazolines were synthesized by the reactions of (NO)2[SnCl6] with arylcyclopropanes containing donor substituents in the aromatic ring.

Δ2-isoxazolines from arylcyclopropanes: III. Phenylcyclopropanes substituted in three-membered ring in reaction with nitrosyl chloride activated with oxides of sulfur(IV, VI)

The reaction of phenylcyclopropanes substituted in the three-membered ring with nitrosyl chloride activated with sulfur(IV, VI) oxides provided in good yield substituted 5-phenylisoxazolines as a mixture of structural isomers.

Solid-phase synthesis of pyrazolines and isoxazolines with sodium benzenesulfinate as a traceless linker

(Matrix presented) The preparation of pyrazoline and isoxazoline derivatives with traceless solid-phase sulfone linker strategy is described. Key steps involved in the solid-phase synthetic procedure include (i) sulfinate S-alkylation, (ii) sulfone anion alkylation, (iii) γ-hydroxy sulfone → γ-ketosulfone oxidation, and (iv) traceless product release via elimination-cyclization. A library of 12 pyrazolines and isoxazolines was synthesized.

Synthesis of 4,5-dihydroisoxazoles from arylcyclopropanes and nitrosyl chloride

Arylcyclopropanes readily react with nitrosyl chloride in liquid sulfur dioxide to give the corresponding 5-aryl-4,5-dihydroisoxazoles in good yield. The reaction is most selective at -40 to -50°C; at higher temperature, the contribution of side processes