N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia.
Molecules. 2022 Dec 21;28(1):64. doi: 10.3390/molecules28010064.
Chromeno[2,3-]pyridines are substances demanded in medicinal and material chemistry. (pot, atom, and step economy) and in particular approaches are key green chemistry techniques that are applied for the synthesis of heterocyclic compounds. In this case, the approach was extended with 'component economy', as solvent was used also as reactant (solvent-involved reaction). This approach was adopted for the synthesis of previously unknown -substituted 5-alkoxy-5-chromeno[2,3-]pyridines via transformation, namely the reaction of salicylaldehydes and malononitrile dimer, with the subsequent addition of alcohol. The mechanistic studies revealed the possibility of concurrent reaction. The studies aided in optimizing the reaction conditions for the best yields (77-93%). Thus, the reaction proceeds efficient and quickly, and the work-up procedure (only simple filtering) is very convenient. The structure of synthesized chromeno[2,3-]pyridines was confirmed by 2D NMR spectroscopy.
色烯并[2,3-c]吡啶类化合物是医药和材料化学领域所需要的物质。(原子经济性、步骤经济性和组分经济性),特别是绿色化学技术中的方法被应用于杂环化合物的合成。在这种情况下,方法扩展到了“组分经济性”,因为溶剂也被用作反应物(溶剂参与的反应)。这种方法被用于通过[2,3-c]吡啶类化合物的转化来合成以前未知的-取代的 5-烷氧基-5-色烯[2,3-c]吡啶,即水杨醛和丙二腈二聚体的反应,随后加入醇。机理研究揭示了并发反应的可能性。这些研究有助于优化反应条件以获得最佳收率(77-93%)。因此,反应高效快速进行,后处理步骤(只需简单过滤)非常方便。通过二维 NMR 光谱确认了所合成的色烯并[2,3-c]吡啶类化合物的结构。