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
Schlagworte:	Chemical Sciences
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container_issue	4
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container_title	Journal of organic chemistry
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creator	Galibert-Guijarro, Aurélien Mouysset, Dominique Mimoun, Liliane Bertrand, Michèle P. Feray, Laurence
description	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.
doi_str_mv	10.1021/acs.joc.2c02906
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title	Ynamides in Radical Reactions: A Route to Original Persubstituted 2‑Aminofurans
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