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• W2509594038 endingPage "4655" @default.
• W2509594038 startingPage "4643" @default.
• W2509594038 abstract "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 CuII and 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." @default.
• W2509594038 created "2016-09-16" @default.
• W2509594038 creator A5029949432 @default.
• W2509594038 creator A5033248021 @default.
• W2509594038 creator A5070955159 @default.
• W2509594038 creator A5090263138 @default.
• W2509594038 date "2016-08-26" @default.
• W2509594038 modified "2023-10-17" @default.
• W2509594038 title "Competitive Copper Catalysis in the Condensation of Primary Nitro Compounds with Terminal Alkynes: Synthesis of Isoxazoles" @default.
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• W2509594038 doi "https://doi.org/10.1002/ejoc.201600897" @default.
• W2509594038 hasPublicationYear "2016" @default.

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