Institute of Chemistry, N.G. Chernyshevsky Saratov National Research State University, 83 Ulitsa Astrakhanskaya, 410012 Saratov, Russia.
Institute of Biochemistry and Physiology of Plants and Microorganisms-Subdivision of the Federal State Budgetary Research Institution Saratov Federal Scientific Centre of the Russian Academy of Sciences (IBPPM RAS), 13 Prospekt Entuziastov, 410049 Saratov, Russia.
Molecules. 2023 Jan 18;28(3):963. doi: 10.3390/molecules28030963.
We describe a method to synthesize a new class of hetarylaminomethylidene derivatives of furan-2(3)-ones. The method uses 5-(4-chlorophenyl)furan-2(3)-one, triethyl orthoformate, and heterocyclic amines with different ring sizes and heteroatoms under refluxing in absolute isopropyl alcohol. The obtained enamines exist in an equilibrium of - and -isomers, whose configurations relative to the double exocyclic C=C bond were confirmed with a set of NMR spectroscopy data. The -/-equilibrium of the synthesized compounds is affected by the configuration of the intermediate, the volume of its substituents, the site of enolate attack, the presence of intramolecular interactions of amino components, the time of the transformation, the order of mixing of the initial reagents, and the use of polar solvents in the NMR experiment. The advantages of the method are that the reaction time is short, the product yield is high, and product purification is easy.
我们描述了一种合成呋喃-2(3)-酮杂芳亚甲基衍生物的新方法。该方法使用 5-(4-氯苯基)呋喃-2(3)-酮、三乙基原甲酸酯和不同环大小和杂原子的杂环胺，在绝对异丙醇回流下进行反应。得到的烯胺以 - 和 - 异构体的平衡形式存在，其相对于双外消旋 C=C 键的构型通过一组 NMR 光谱数据得到确认。合成化合物的 -/- 平衡受到中间体的构型、取代基的体积、烯醇化物攻击的位置、氨基成分的分子内相互作用的存在、转化时间、初始试剂混合顺序以及在 NMR 实验中使用极性溶剂的影响。该方法的优点是反应时间短，产物收率高，产物易于纯化。
