4264-05-5

Usage

Synthesis Reference(s)

Synthesis, p. 612, 1976 DOI: 10.1055/s-1976-24140

Upstream product

• 1006-65-1 3-phenylisoxazole 
• 108-05-4 vinyl acetate 
• 1011-84-3 4-nitrobenzohydroximoyl chloride 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 2574-03-0 p-nitrobenzonitrile oxide 
• 112853-64-2 3-(4-nitrophenyl)-5-hydroxy-4,5-dihydroisoxazole 
• 947-57-9 dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate 
• 19019-88-6 7-isopropylidene-2,3-dicarbomethoxynorbornadiene 
• 35167-28-3 vinyl phenyl selenide 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1734-79-8 3-(4-nitrophenyl)-2-propenal 

Downstream Products

• 34614-63-6 3-(2,4-dinitro-phenyl)-4-nitro-isoxazole 
• 765912-47-8 4-(isoxazol-3-yl)aniline 

Relevant academic research and scientific papers

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 synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols

"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.

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.

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

ANTIBACTERIAL 1, 3- OXAZOLIDIN -2- ONE DERIVATIVES

Compounds of the formula (I), or a pharmaceutically-acceptable salts, or in-vivo-hydrolysable esters thereof, wherein: N-HET is for example triazolyl substituted with R1; R1 is for example optionally substituted (1-4C)alkyl; Q is for

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.

SYNTHESIS OF 3-ARYL-4,5-DIHYDRO-5-HYDROXY-1,2-OXAZOLES BY REACTION OF SUBSTITUTED BENZONITRILE OXIDES WITH THE ENOLATE ION OF ACETALDEHYDE.

By reaction of substituted benzonitrile oxides with the enolate ion of acetaldehyde (quantitatively generated by the known cycloreversion of THF in the presence of n-butyllithium) a number of 3-aryl-4,5-dihydro-5-hydroxy-1,2-oxazoles (previously unknown or, in two cases, only synthesized by different procedures) have been isolated in high yields.Treatment of such hydroxy-isoxalines with some common bases allows their conversion in high yields into the corresponding isoxazoles.

4,5-DIHYDROISOXAZOLES. IV. 4- AND 5-PHENYLTHIO-4,5-DIHYDROISOXAZOLES AND THEIR BEHAVIOUR WITH PERFORMIC ACID

Several cis- and trans-4,5-dihydroisoxazole derivatives bearing a phenylthio group on C(4) or C(5) have been prepared by cyclo-addition of the corresponding unsaturated sulphides and nitrile oxides.The cyclo-adducts have been oxidized by HCOOH/H2O2.It has been shown that this oxidation leads mainly to isoxazole derivatives (i.e. is accompanied by elimination) when the sulphur-containing substituent is bound to C(5).The 4-phenylthio-substituted regioisomers gave in most cases the corresponding sulphones.

SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES

The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.