3672-52-4

Usage

InChI:InChI=1/C16H13NO2/c1-18-14-9-7-12(8-10-14)15-11-16(19-17-15)13-5-3-2-4-6-13/h2-11H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 6327-79-3 1-(4-methoxyphenyl)-3-phenylpropane-1,3-dione 
• 2475-92-5 4-methoxyacetophenone oxime 
• 20080-08-4 3-(4-methoxyphenyl)-5-phenyl-4,5-dihydroisoxazole 
• 132971-99-4 (Z)-2-bromo-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 67-56-1 methanol 
• 64-19-7 acetic acid 
• 536-74-3 phenylacetylene 
• 15500-73-9 4-methoxybenzonitrile oxide 
• 20442-66-4 3-(4-methoxyphenyl)-1-phenylprop-2-yn-1-one 
• 1004-22-4 (phenylethynyl)sodium 
• 38435-51-7 N-hydroxy-4-methoxy-benzenecarboximidoyl chloride 
• 17064-22-1 2-(4-methoxyphenyl)-5-phenyl oxazole 

Downstream Products

• 80223-00-3 3-(4-Methoxy-phenyl)-2-methyl-5-phenyl-isoxazol-2-ium; iodide 
• 22439-72-1 3-(4-hydroxyphenyl)-5-phenylisoxazole 
• 70312-74-2 1-(2,2-diphenyl-ethenesulfonyl)-4-methyl-benzene 

Relevant academic research and scientific papers

3, 5-disubstituted isoxazole derivative and synthesis method thereof

The invention provides a 3, 5-disubstituted isoxazole derivative and a synthesis method thereof, and belongs to the technical field of organic synthesis medicines and medical intermediates. The method comprises the following steps: adding a proper solvent

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

Complementary and Regioselective Synthesis of Isomeric 3-[Isoxazol-3(or 5)-yl]indoles from β-Ethylthio-β-indolyl-α,β-unsaturated Ketones

A simple and efficient method for the complementary and regioselective synthesis of isomeric 3-(isoxazol-5-yl)indoles and 3-(isoxazol-3-yl)indoles has been developed by the regioselective cyclocondensation reaction of β-ethylthio-β-indolyl-α,β-unsaturated ketones and hydroxylamine hydrochloride. It was found that the cyclocondensation reaction in the presence of excess NaOEt in refluxing EtOH gives 3-(isoxazol-5-yl)indoles in good yields, whereas using NaOAc in boiling AcOH gives 3-(isoxazol-3-yl)indoles in good yields.

Green preparation method of isoxazole compound participating in water-soluble vitamin E

The invention provides a green synthesis method of an isoxazole compound represented by the formula (III), wherein the aldehyde oxime compound represented by the formula (I) is a substrate and is in an aqueous solution of a surfactant with a mass concentration 1 wt % - 5 wt % in N - chlorosuccinimide. The alkyne compound represented by the formula (II) is reacted 6 - 16h at room temperature under the common action of the basic substance, and the resulting reaction solution is post-treated to obtain the isoxazole compound represented by the formula (III). Water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized.

Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation

An efficient new synthesis of 3,5-bis(het)arylisoxazoles, involving the reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide in the presence of IBX catalyst, has been reported. The reaction proceeds at room temperature in high yields and is applicable to a broad range of substrates including the synthesis of 5-methyl-3-arylisoxazoles, a key subunit present in several β-lactamase-resistant antibiotics. A probable mechanism for the formation of isoxazoles has been suggested. A few of the 5-styryl/arylbutadienyl-3-(het)arylisoxazoles have also been synthesized by reacting the corresponding 1-(het)aryl-1-(methylthio)-4-(het)arylidene-but-1-en-3-ones with sodium azide at higher temperatures. The reaction of β-ketodithioesters with sodium azide is shown to furnish β-ketonitriles in good yields.

Unusual Reactivity of 4-Vinyl Isoxazoles in the Copper-Mediated Synthesis of Pyridines, Employing DMSO as a One-Carbon Surrogate

An efficient protocol for the synthesis of nicotinate derivatives and tetrasubstituted pyridines through a copper-mediated cleavage of isoxazoles has been developed. The highlight of the work is the observation of an unusual reactivity of 4-vinyl isoxazoles under the reaction conditions. DMSO serves as a one-carbon surrogate generating an active methylene group during the reaction to form two C-C bonds. This protocol provides a facile and an expeditious approach for the assembly of densely substituted N-heterocyclic compounds.

Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes

A rhodium-catalyzed cascade annulative coupling of 3,5-diarylisoxazoles with three equivalents of an alkyne proceeds smoothly in the presence of a Cu(II) oxidant, where the sequential construction of isoquinoline and naphtho[1,8- bc ]pyran frameworks connected by a biaryl linkage is achieved by a single operation. Most of the obtained polycyclic compounds exhibit visible fluorescence in both the solution and the solid state. The hexaphenylated isoquinoline-naphthopyran conjugate (R = Ph) as a representative product shows a green emission which can be turned off by making an isoquinolinium salt with an acid. The emission is also reversibly turned on by treatment with a base.

Trichloroisocyanuric acid mediated one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones

A facile one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones and hydroxylamine hydrochloride is reported. The reaction is efficiently promoted by trichloroisocyanuric acid (TCCA) to afford the desired products, mostly in high yields and

A convenient one-pot synthesis of 3,5-diarylisoxazoles via oxidative cyclisation using catalytic CuBr2 and oxone

A facile one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones and hydroxylamine hydrochloride is reported. The reaction is efficiently promoted by catalytic CuBr2 and Oxone to afford the desired products mostly in high yields

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.