合成 5-(4-甲酰基苯基)巴比妥酸以获得可烯醇化的铬代巴比妥酸

IF 2 Q2 CHEMISTRY, ORGANIC
SynOpen Pub Date : 2024-09-02 DOI:10.1055/s-0043-1775398
Alexander Schade
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引用次数: 0

摘要

单取代 5 位的巴比妥酸会出现酮烯醇同分异构现象。在酮形式中,由于巴比妥酸 5 位上的 sp³ 杂化碳原子,与芳基取代基的共轭被中断。烯醇形式会产生一个与芳基取代基共轭的 π-系统,并作为一个电子奉献基团。如果芳基取代基是缺电子的,则会产生一个推拉系统,显示典型的紫外/可见吸收。由于其固有的可转换性,很难合成这类化合物。本文报道了在 5 位上具有 4-甲酰基苯基官能团的巴比妥酸的合成。这种名为 5-(4-甲酰基苯基)巴比妥酸的化合物可通过简单的缩合反应,引入具有多种电子抽出基团的扩展 π 系统。我们通过霍纳-沃兹沃斯-埃蒙斯反应证明了这一点,该反应生成了可烯醇化的染料 (E)-5-(4-(4-硝基苯基)苯基)巴比妥酸。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis of 5-(4-Formylphenyl)barbituric Acid to Access Enolizable Chromophoric Barbituric Acids

Synthesis of 5-(4-Formylphenyl)barbituric Acid to Access Enolizable Chromophoric Barbituric Acids

Barbituric acids mono-substituted at the 5-position show keto–enol tautomerism. In the keto form, conjugation to an aryl substituent is interrupted due to the sp³-hybridized carbon atom at the 5-position of barbituric acid. The enol form generates a conjugated π-system to the aryl substituent and acts as an electron-donating group. If the aryl substituent is electron-deficient, a push-pull system is generated that shows typical UV/Vis absorption. These types of compounds are difficult to access synthetically due to their intrinsic convertibility. The synthesis of barbituric acids with a 4-formylphenyl functionality at the 5-position is reported. This compound, 5-(4-formylphenyl)barbituric acid, could be used to introduce extended π-systems with electron-withdrawing groups in great variety by simple condensation reactions. We demonstrate this by a Horner–Wadsworth–Emmons reaction that forms the enolizable dye (E)-5-(4-(4-nitrostyryl)phenyl)barbituric acid.

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来源期刊
SynOpen
SynOpen CHEMISTRY, ORGANIC-
CiteScore
2.30
自引率
4.00%
发文量
35
审稿时长
6 weeks
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