Insights into the triple self-condensation reaction of thiophene-based methyl ketones and related compounds
作者:Anita Andicsová-Eckstein、Daniel Végh、Alžbeta Krutošíková、Zita Tokárová
DOI:10.24820/ark.5550190.p010.516
日期:——
The acid catalysed triple self-condensation of 1-thien-2-ylethanone (2-acetylthiophene) and five related compounds is presented. Tetrachlorosilane used as the Lewis acid produces dry hydrogen chloride which catalyzes the self-condensation process. Depending on the reaction conditions and the substitution of the carbonyl substrates, the reaction can proceed as a [2+2+2] cyclotrimerization towards C3-symmetric
介绍了酸催化的 1-thien-2-ylethanone(2-乙酰噻吩)和五种相关化合物的三重自缩合。用作路易斯酸的四氯硅烷产生干燥的氯化氢,其催化自缩合过程。根据反应条件和羰基底物的取代,反应可以作为 [2+2+2] 环三聚向 C3 对称的 1,3,5 三取代苯进行,或作为导致 1, 3-二取代 (E)-β-甲基查耳酮。这对于设计超出模型结构的新芳香族/烯烃化合物很重要。讨论了使用三氟甲磺酸铒通过混合型羟醛反应合成 4'-氟-3,5-二-(2-噻吩基) 联苯。提供了机械原理。