13271-86-8

Upstream product

• 5868-55-3 (3-p-tolyl-isoxazol-5-yl)-boronic acid 
• 3235-02-7 p-methylbenzaldehyde oxime 
• 1021942-52-8 (Z)-3-bromo-3-(p-tolyl)acrylaldehyde 
• 40808-08-0 (Z)-3-chloro-3-(p-tolyl)acrylaldehyde 
• 521075-51-4 3-(4-methylphenyl)-2H-azirine-2-carboxaldehyde 
• 1504-75-2 3-(4-methylphenyl)acrylaldehyde 
• 1606167-98-9 C₁₅H₁₄NO⁽¹⁺⁾*Br^(1-) 
• 13820-14-9 4-methylbenzonitrile oxide 
• 122058-30-4 p-methylcinnamyl alcohol 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 36288-37-6 N-hydroxy-4-methylbenzenecarboximidoyl chloride 
• 35167-28-3 vinyl phenyl selenide 
• 521075-48-9 (Z)-3-azido-3-(4-methylphenyl)prop-2-en-1-ol 
• 13271-87-9 3-(p-tolyl)-5-acetoxy-4,5-dihydroisoxazole 

Downstream Products

• 104-85-8 para-methylbenzonitrile 
• 169547-67-5 3-(4-(bromomethyl)phenyl)isoxazole 

Relevant academic research and scientific papers

Reactions of trans-1-(β-aroylvinyl)pyridinium bromides with hydroxylamine hydrochloride

Reactions of trans-1-(β-aroylvinyl)pyridinium bromides with hydroxylamine hydrochloride lead to a mixture of substituted isoxazoles regardless of the substituent nature in the aromatic core and the solvent.

Polymer-supported vinyl sulfone as an efficient reagent for the synthesis of 3-monosubstituted isoxazoles

Polystyrene-supported vinyl sulfone reagent has been developed and used for solid-phase organic synthesis of 3-monosubstituted isoxazoles by 1,3-dipolar cycloaddition reaction with nitrile oxides and subsequent cleavage from the polymer support through an

Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles

(Figure Presented) A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild conditions, high regioselectivity, and wide scope.

Synthesis of azirines containing aldehyde functionality and their utilization as synthetic tools for five membered oxazoles and isoxazoles

(Chemical Equation Presented) A simple and useful procedure for the synthesis of azirines containing aldehyde functionality from open chain bromo/chloro-aldehydes at room temperature is reported. The scope of the ring expansion reaction of a number of 3-s

Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA

3-Arylisoxazoles react with LDA in THF at 0 °C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A?fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA.

Stereoselective dimerization of 3-arylisoxazoles to cage-shaped bis-β-lactams syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by hindered lithium amides

3-Arylisoxazoles react with hindered lithium amides giving syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones in good to fair yields. Stereochemistry of the so-obtained cage-shaped bis-β-lactams was assigned by X-ray diffraction analysis. Concerning the mechanism of formation of such hitherto unknown molecules, dimerization of an azetinone anion intermediate stereoselectively induced by Li+ chelation is suggested.

Traceless solid-phase synthesis of 3-substituted isoxazoles and 3-substituted 5-iodoisoxazolines using polystyrene-supported vinyl selenide

A novel facile procedure for the traceless solid-phase synthesis of 3-substituted isoxazoles and 3-substituted 5-iodoisoxazolines in good yields and with excellent purities using polymer-supported vinyl selenide is described. The polymeric reagent can be

Substituent effects on 15N and 13C NMR chemical shifts of 3-phenylisoxazoles: A theoretical and spectroscopic study

The synthesis and assignment of 15N and 13C NMR signals of the isoxazole ring in a series of parasubstituted 3-phenyl derivatives are reported. DFT calculations of 15N and 13C chemical shifts are presented and c

A convenient and expedient synthesis of 3-aryl-2H-azirine-2-carboxaldehydes

A new procedure for the synthesis of 3-aryl-2H-azirine-2-carboxaldehydes starting from cinnamyl alcohols is disclosed. This novel approach implies milder conditions and higher overall yields as compared to the previously reported methods. The key step, i.e. the formation of the azirine ring, involves the treatment of (Z)-3-aryl-3-azidoprop-2-en-1-ols with MnO2.

One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide

Phenyl vinylic selenide was adopted for 1,3-dipolar cycloaddition to nitrile oxides and subsequent oxidation-elimination furnished 3-substituted isoxazoles with good yields in a one-pot, two-step transformation.