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
Hauptverfasser: Galibert-Guijarro, Aurélien, Mouysset, Dominique, Mimoun, Liliane, Bertrand, Michèle P., Feray, Laurence
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02906