Department of Organic Synthesis & Process Chemistry CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
J Org Chem. 2023 Jun 2;88(11):7046-7057. doi: 10.1021/acs.joc.3c00315. Epub 2023 May 12.
The reaction of alkynyl -quinone methide (QM) with keto-methylenes through a base-mediated tandem 1,6-addition/annulation sequence, [2 + 3] annulation, affording the furans is reported for the first time. A variety of functionalized furans, including fused derivatives, were obtained in good to excellent yields under mild reaction conditions. The efficacy of alkynyl QMs is highlighted by extending their use to access isoxazoles, pyrazoles [3 + 2] annulation, and pyridines through [3 + 3] annulation in the presence of different bis-nucleophiles.
炔基-醌甲化物（QM）与酮亚甲基通过碱介导的串联 1,6-加成/环化序列反应，[2 + 3]环化，首次报道了呋喃的反应。在温和的反应条件下，通过多种官能化呋喃，包括稠合衍生物，以良好至优异的收率获得。炔基 QM 的功效通过在不同双亲核试剂存在下通过[3 + 3]环化来扩展其用途以获得异恶唑、吡唑[3 + 2]环化和吡啶而得到强调。
