通过无催化剂多米诺反应前所未有地合成吲哚连接的四取代烯烃

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-10-24 DOI:10.1016/j.tet.2024.134327
Darakshan, Ujjain Chaurasia, Aatka Mehar, Tasneem Parvin
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引用次数: 0

摘要

在此,我们报告了一种简单、高效、无催化剂的绿色多米诺反应,该反应在 100 °C、二甲基甲酰胺介质中露天条件下进行,反应物包括吲哚、芳基乙二醛和环状 1,3-二羰基(如巴比妥酸衍生物/二甲酮)。在该反应中,无需使用任何添加剂或金属试剂,就能在一锅中形成一个 C-C 键和一个 CC 键。考虑到产品中存在吲哚、苯甲酰基和环 1,3-二羰基,预计它们将表现出有趣的药用特性。所有合成产品都通过傅立叶变换红外光谱、1H NMR、13C NMR 和 HRMS 进行了表征。此外,还记录了化合物 4j 的单晶 XRD,以确认产品的结构。该方法操作简单、合成规模为克级、反应条件温和、产率高、底物范围广是其显著特点。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Unprecedented synthesis of indole-linked tetra-substituted alkenes by catalyst-free domino reaction
Herein, we report a simple, efficient catalyst-free green domino reaction of indole, arylglyoxal, and cyclic 1,3-dicarbonyls such as barbituric acid derivatives/dimedone at 100 °C in dimethylformamide medium in open air condition. In this reaction, one C–C and one CC bonds have been formed in one-pot without using any additive or metal based reagent. Considering the presence of indole, benzoyl and cyclic 1,3-dicarbonyl moieties in the products, it is expected that they will exhibit interesting medicinal properties. All the synthesized products were characterized by recording FTIR, 1H NMR, 13C NMR, and HRMS. Moreover, a single crystal XRD of compound 4j was recorded to confirm the structure of the product. Operational simplicity, gram-scale synthesis, mild reaction conditions, good yields, and wide substrate scope are the salient features of this methodology.
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
期刊最新文献
Editorial Board Contents continued Graphical abstract TOC Graphical abstract TOC Transition metal-catalyzed P(O)–H alkenylation, allenylation and alkynylation reactions: A recent trend
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