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A TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles was developed, providing 3,5-diarylisoxazoles in good yields. Functional groups such as methoxy, ethyoxyl, chloro, bromo, fluoro and nitro were well tolerated in this reaction. Notably, the reaction ran under metal-free in water.

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Isoxazole – Wikipedia,
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The relative reaction rate of five-membered heterocycles with ozone was evaluated.These relative rates were correlated to the highest bond order value in the corresponding ring, calculated by the convenient HMO model.From this correlation, the reactivity of heterocycles with ozone was able to be predicted.Also it was concluded that the predominant product in the ozonolysis of five-membered heterocycles containing an oxygen atom was the corresponding carboxylic acid, while nitrogen heterocycles gave the corresponding amide.

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N-Iodosuccinimide has been successfully employed as an oxidative cyclising agent for the synthesis of oxazole, isoxazole, benzofuran, furoxan and 1,2,3-triazole-1-oxide derivatives.Synthesis of compounds (II), (IV), (VI), (VIII) and (X) having these basic skeletons respectively are reported.

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Dioximes of 1,3-diketones enter into the Trofimov reaction forming pyrroles containing an acyl or an O-vinyloxime substituent in position 3 of the pyrrole. In the case of sterically hindered dioximes the main reaction products are isoxazoles. 2005 Springer Science+Business Media, Inc.

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The reactions of the 3-methyl group in 5-aryl-2,3-dimethylisoxazolium tetrafluoroborates with aromatic aldehydes, in the presence of piperidine were studied. Isoxazolium salt reactivity is independent of the phenyl group substituent at C-5 on the isoxazolium salt ring. However, it does depend on the aldehyde structure.

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A series of 5-arylisoxazole derivatives were synthesized via the reaction of 3-(dimethyl-amino)-1-arylprop-2-en-1-ones with hydroxylamine hydrochloride in aqueous media without using any catalyst. This method has the advantages of easier work-up, mild reaction conditions, high yields, and an environmentally benign procedure.

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1,3-Dipolar cycloaddition reaction of trimethylstannylacetylene with nitrile oxides yielded 3-substituted 5-(trimethylstannyl)isoxazoles. On the other hand, the same reaction of (trimethylstannyl)phenylacetylene, -1-hexyne, and -(trimethylsilyl)acetylene gave 3,5-disubstituted 4-(trimethylstannyl)isoxazoles almost regioselectively. The regioselectivity of the cycloaddition reaction is interpreted by application of the frontier-electron theory.

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The synthesis of (isoxazol-4-ylmethyl)triphenylphosphonium salts derived from 5-alkyl- and 5-aryl-3-methylisoxazoles has been carried out. This method involves the preparation of several 4-(chloromethyl)isoxazoles which are suitable precusors for these phosphonium salts. The phosphonium salts were completely characterized by spectroscopic methods and were obtained in very good to quantitative yields.

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5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.

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Reaction of several alpha,beta-unsaturated ketoximes with N-bromosuccinimide (NBS) gave isoxazoles, but yields were lower and the reaction less general than a similar transformation using iodine under basic conditions.With beta,beta-disubstituted oximes, 4-halo-5,5-disubstituted-2-isoxazolines were obtained using NBS, iodine, or N-chlorosuccinimide.Treatment of the 4-bromoisoxazolines with silver acetate or silver nitrate caused either elimination with rearrangement to give isoxazoles or substitution at C-4, depending upon the nature of the substituents at C-5.

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