25388-20-9

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 7063-95-8 acetonitrile-N-oxide 
• 3356-93-2 5-bromo-3-methyl-4-phenyl-isoxazole 
• 79-24-3 Nitroethane 
• 536-74-3 phenylacetylene 
• 673-32-5 1-Phenylprop-1-yne 
• 119072-55-8 tert-butylisonitrile 
• 25388-08-3 5-hydrazino-3-methyl-4-phenyl-isoxazole 
• 17019-26-0 (E)-2-(hydroxyimino)-1-phenylpropan-1-one 
• 25632-68-2 3-methyl-4-phenylisoxazol-5(4H)-one 
• 148343-07-1 C₂₀H₂₇N₃O₆ 
• 591-50-4 iodobenzene 
• 3356-91-0 5-chloro-3-methyl-4-phenyl-isoxazole 
• 60239-09-0 3-methyl-4-phenylisoxazoline 2-oxide 

Downstream Products

• 28867-78-9 (Z)-1-phenyl-1,2-propanedione 2-oxime 
• 17019-26-0 (E)-2-(hydroxyimino)-1-phenylpropan-1-one 

Relevant academic research and scientific papers

Synthesis and reactions of 4-tributylstannyl-3-methylisoxazole

1,3-Dipolar cycloaddition reaction of bis(tributylstannyl)acetylene with nitrile oxides, followed by treatment with aqueous ammonia in ethanol in a sealed tube gave 4-tributylstannyl-3-methylisoxazole. The palladium catalyzed cross coupling reaction of the isoxazole with 2-iodonitrobenzene, followed by reductive cyclization afforded 3-acetylindole.

Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles

Isoxazoles, mainly 3,5-disubstituted, are prepared by catalytic condensation of primary nitro compounds with terminal acetylenes by using a copper/base catalytic system. The additional catalytic effect of the copper(II) salts is evidenced by comparing the kinetic profiles. Selectivity dependence on reaction conditions is considered for phenylacetylene in the following competitive processes: oxidative coupling of terminal alkynes to conjugated diynes catalyzed by CuIIand base in the presence of air; production of furazans beside condensation with benzoylnitromethane to 3-benzoylisoxazoles, as a result of the reaction of the dipolarophile with 3,4-dibenzoylfuroxan; addition of electron-poor alkynes (e.g., methyl propiolate) with themselves and with the nitro compound. Thus, oxidative coupling is negligible in reactions with “active” nitro compounds, whereas with nitroalkanes both products are observed: only trace amounts of isoxazoles are detected without copper. Similarly, in the presence of copper, 3-benzoyl-5-phenylisoxazole is predominant over the furazan. Furthermore, condensations of electron-poor alkynes give complex reaction mixtures in the presence of base alone, but cycloadducts are conveniently prepared with copper. The results indicate the practical and general utility of this catalytic method for synthetic practice.

Regioselective conversion of alkynes to 4-substituted and 3,4-disubstituted isoxazoles using titanium-catalyzed multicomponent coupling reactions

Conditions have been developed for the regioselective synthesis of 4-substituted isoxazoles from terminal alkynes and 3,4-disubstituted isoxazoles from internal alkynes. The methodology involves a one-pot titanium-catalyzed multicomponent coupling reactio

Oxazolo[4,5-d]isoxazole derivatives and 3,4-disubstituted isoxazoles from isoxazol-5(4H)-ones

Synthesis for oxazolo[4,5-d]isoxazole derivatives and 3,4-disubstituted isoxazoles from isoxazol-5(4H)-ones is reported.

An Improved Preparation of 5-Unsubstituted Isoxazoles by Borohydride Reduction of 5-Chloroisoxazoles

The borohydride reduction of 5-chloroisoxazoles offersa useful and unambiguous way to 5-unsubstituted isoxazoles.

REGIOSELECTIVE CYCLOADDITION REACTIONS OF ALLYLSILANES AND SILYL ENOL ETHERS WITH NITRONES AND NITRILE OXIDES. SYNTHESIS OF HOMOALLYLAMINES

Allylsilanes and silyl enol ethers add to nitrones and nitrile oxides regioselectively to give the corresponding isoxazolidines and isoxazolines in good yield.Hydrogenative cleavage of the N-O bond of cycloadducts with allylsilanes affords homoallyl

S-Ethenylsulfoximine Derivatives. Reagents for Ethylenation of Protic Nucleophiles

The preparation of S-vinyl and S-(2-substituted)ethenyl derivatives of sulfoximines is described.Vinyl-, (2-phenylethenyl)-, (2,2-diphenylethenyl)-, (2-methyl-1-propenyl)-, (dimethylamino)phenyloxosulfonium fluoroborates were found to undergo an addition-elimination reaction sequence with protic nitrogen and carbon nucleophiles, resulting in ethylenation of the nucleophile and N,N-dimethylbenzenesulfinamide.Primary amines gave aziridines, enamines gave cyclopropyl derivatives of iminium salts or pyrrolidinium salts, anions of active methylene compounds gave dihydrofurans and/or cyclopropanes, and anions of nitroalkanes gave cyclic nitronic esters and/or nitrocyclopropanes.In several cases vinyl salts were generated in situ from β-methoxyoxosulfonium salts.Treatment of (-)-(S)-dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate with methyl cyanoacetate in methanol containing sodium methoxide gave, in 81percent yield, (+)-(1S,2R)-methyl 1-cyano-2-phenylcyclopropanecarboxylate of 25.5percent optical purity.The same salt upon treatment with methyl nitroacetate gave, in 95percent yield, methyl 4-phenyl-3-isoxazolinecarboxylate 2-oxide with 33percent enantiomeric excess.Cyclopropanes were formed upon treatment of S-methyl-S-(trans-2-phenylethenyl)-N-(p-tolylsulfonyl)sulfoximine with anions of active methylene compounds.