Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)- para -Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds

作者：Zong‐Wang Qiu, Xue-Tao Xu, Han‐Peng Pan, Zhen‐Sheng Jia, Ai‐Jun Ma, Jin‐Bao Peng, Ji‐Yuan Du, Na Feng, Bao Qiong Li, Xiang‐Zhi Zhang · 发表于：The Journal of Organic Chemistry · 年份：2021 · DOI：10.1021/acs.joc.0c02844 · 被引用次数：21 · 研究领域：Synthesis of Indole Derivatives、Sulfur-Based Synthesis Techniques、Multicomponent Synthesis of Heterocycles

Herein, we describe a highly effective 1,8-conjugate-addition-mediated formal (3+3)-annulation of (aza)- para -quinone methides in situ generated from propargylic alcohols with 4-hydroxycoumarins and 1,3-dicarbonyl compounds under the catalysis of a Brønsted acid. This methodology affords efficient and practical access to synthetically important and highly functionalized pyranocoumarins and pyrans in excellent yields under mild conditions. Importantly, these products exhibit impressive inhibitory activity toward α-glucosidase.