Department of General and Inorganic Chemistry, University of Pécs, Ifjúság útja 6., H-7624 Pécs, Hungary.
HUN-REN-PTE Research Group for Selective Chemical Syntheses, Ifjúság útja 6., H-7624 Pécs, Hungary.
Int J Mol Sci. 2024 Sep 20;25(18):10128. doi: 10.3390/ijms251810128.
A library of C-3 functionalized flavones was successfully provided via palladium-catalyzed amino- and aryloxycarbonylation reactions of 3-iodoflavone (), under mild conditions. This methodology showed good functional group tolerance using a variety of amines and phenols, under an atmospheric pressure of carbon monoxide as a carbonyl source. While the flavone-3-carboxamides () were produced in 22-79%, the flavone-3-carboxylates () were obtained in excellent yields (up to 88%), under identical reaction conditions, just by switching -nucleophiles to -nucleophiles. The convenient availability of the involved starting materials confers simplicity to this approach to design new C-3-substituted flavones of biological relevance. The solid-state structures of flavone-3-carboxamide () and flavone-3-ester () were further studied by single-crystal XRD analysis.
通过钯催化的 3-碘黄酮（）的氨基和芳氧基羰基化反应，成功地提供了 C-3 功能化黄酮库，反应条件温和。该方法在一氧化碳的大气压力下作为羰基源，使用各种胺和酚类化合物具有良好的官能团耐受性。当酰胺（）的产率为 22-79%时，在相同的反应条件下，只需将亲核试剂从 -亲核试剂切换为 -亲核试剂，就可以获得 3-羧酸酯（），产率优异（高达 88%）。所涉及起始材料的方便可用性使这种设计具有生物相关性的新型 C-3 取代黄酮的方法变得简单。通过单晶 XRD 分析进一步研究了黄酮-3-酰胺（）和黄酮-3-酯（）的固态结构。
