Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
HUN REN SZTE Stereochemistry Research Group, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.
Int J Mol Sci. 2024 Jun 26;25(13):6966. doi: 10.3390/ijms25136966.
Alkoxyalkylation and hydroxyalkylation methods utilizing oxo-compound derivatives such as aldehydes, acetals or acetylenes and various alcohols or water are widely used tools in preparative organic chemistry to synthesize bioactive compounds, biosensors, supramolecular compounds and petrochemicals. The syntheses of such molecules of broad relevance are facilitated by acid, base or heterogenous catalysis. However, degradation of the -analogous Mannich bases are reported to yield alkoxyalkyl derivatives via the -Mannich reaction. The mutual derivative of all mentioned species are quinone methides, which are reported to form under both alkoxy- and aminoalkylative conditions and via the degradation of the Mannich-products. The aim of this review is to summarize the alkoxyalkylation (most commonly alkoxymethylation) of electron-rich arenes sorted by the methods of alkoxyalkylation (direct or via -Mannich reaction) and the substrate arenes, such as phenolic and derived carbocycles, heterocycles and the widely examined indole derivatives.
利用氧代化合物衍生物（如醛、缩醛或炔烃）和各种醇或水的烷氧基烷基化和羟烷基化方法是制备有机化学中合成生物活性化合物、生物传感器、超分子化合物和石油化学品的广泛使用的工具。这些具有广泛相关性的分子的合成可以通过酸、碱或多相催化来促进。然而，据报道，-类似的曼尼希碱的降解会通过-Mannich 反应生成烷氧基烷基衍生物。所有提到的物种的互变异构体都是醌甲亚胺，据报道，它们在烷氧基和氨基烷基化条件下以及通过曼尼希产物的降解下形成。本综述的目的是总结富电子芳环的烷氧基烷基化（最常见的是烷氧基甲基化），按烷氧基烷基化（直接或通过-Mannich 反应）和芳基底物（如酚类和衍生的碳环、杂环以及广泛研究的吲哚衍生物）的方法进行分类。
