Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)-<i>para</i>-Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds
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
Abstract
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.
Topics & Concepts
AnnulationChemistryBrønsted–Lowry acid–base theoryCatalysisConjugateQuinoneCombinatorial chemistryOrganic chemistryMathematical analysisMathematicsSynthesis of Indole DerivativesSulfur-Based Synthesis TechniquesMulticomponent Synthesis of Heterocycles