Ynamides in Radical Reactions: A Route to Original Persubstituted 2‑Aminofurans
Mn(OAc)3/Cu(OAc)2-mediated reaction between ynamides, derived from oxazolidone or 3-methylindole carboxylate, and cyclic α-dicarbonyl radicals led to the one-pot synthesis of 2-aminofurans. The transformation involves addition of the α-dicarbonyl radical to ynamide, oxidation to ketene-iminium, an...
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Veröffentlicht in: | Journal of organic chemistry 2023-02, Vol.88 (4), p.2464-2473 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Mn(OAc)3/Cu(OAc)2-mediated reaction between ynamides, derived from oxazolidone or 3-methylindole carboxylate, and cyclic α-dicarbonyl radicals led to the one-pot synthesis of 2-aminofurans. The transformation involves addition of the α-dicarbonyl radical to ynamide, oxidation to ketene-iminium, and polar cyclization steps to provide original persubstituted 2-aminofurans in good to excellent yields. This work represents the first radical route for the synthesis of furans from ynamides. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.2c02906 |