4 research outputs found

    Synthesis of Spiro-lactams and Polysubstituted Pyrroles via Ceric Ammonium Nitrate-Mediated Oxidative Cyclization of <i>N</i>‑Furan-2-ylmethyl‑β<i>-</i>Enaminones

    No full text
    Spiro-lactams and polysubstituted pyrroles were synthesized by reactions of furfurylamines with ynones followed by oxidation. Specifically, the protocol involved in situ generation of <i>N</i>-furan-2-ylmethyl-β-enaminones and their subsequent oxidation by ceric ammonium nitrate (6 equiv for spiro-lactam formation, 3 equiv for pyrrole formation). This useful dearomatizing oxidation, which likely proceeds via a free-radical pathway, can be expected to extend the synthetic applications of furan and pyrrole derivatives

    Synthesis of Spiro-lactams and Polysubstituted Pyrroles via Ceric Ammonium Nitrate-Mediated Oxidative Cyclization of <i>N</i>‑Furan-2-ylmethyl‑β<i>-</i>Enaminones

    No full text
    Spiro-lactams and polysubstituted pyrroles were synthesized by reactions of furfurylamines with ynones followed by oxidation. Specifically, the protocol involved in situ generation of <i>N</i>-furan-2-ylmethyl-β-enaminones and their subsequent oxidation by ceric ammonium nitrate (6 equiv for spiro-lactam formation, 3 equiv for pyrrole formation). This useful dearomatizing oxidation, which likely proceeds via a free-radical pathway, can be expected to extend the synthetic applications of furan and pyrrole derivatives

    2,5-Oxyarylation of Furans: Synthesis of Spiroacetals via Palladium-Catalyzed Aerobic Oxidative Coupling of Boronic Acids with α‑Hydroxyalkylfurans

    No full text
    A protocol for the 2,5-oxyarylation of furan rings via Pd-catalyzed aerobic oxidative coupling of boronic acids with α-hydroxyalkylfurans is reported. This protocol provides rapid, green access to diverse biologically interesting and synthetically useful unsaturated spiroacetals from sustainable furan derivatives
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