Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2024-09-03 DOI:10.3762/bjoc.20.190

Haifeng Yu, Wanting Zhang, Xuejing Cui, Zida Liu, Xifu Zhang, Xiaobo Zhao

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Abstract

An eco-friendly selective hydrolysis of chain α-oxo ketene N,S-acetals in water for the switchable synthesis of β-keto thioesters and β-keto amides is reported. In refluxing water, the hydrolysis reactions of α-oxo ketene N,S-acetals in the presence of 1.0 equiv of dodecylbenzenesulfonic acid effectively afforded β-keto thioesters in excellent yield, while β-keto amides were successfully obtained in excellent yield when the hydrolysis reactions were carried out in the presence of 3.0 equiv of NaOH. The green approach to β-keto thioesters and β-keto amides avoids the use of harmful organic solvents, thiols and thiolacetates as well as amines, which could result in serious environmental and safety issues.

Abstract Image

Beilstein J. Org. Chem. 2024, 20, 2225–2233. doi:10.3762/bjoc.20.190

查看原文本刊更多论文

α-氧代酮 N,S-乙醛在水中的选择性水解：β-酮硫代酯和β-酮酰胺的可切换水性合成

摘要报告了一种在水中选择性水解链 α-氧代酮 N,S-乙醛以可切换合成 β-酮硫酯和 β-酮酰胺的环保型方法。在回流水中，α-氧代酮 N,S-乙醛在 1.0 等量十二烷基苯磺酸的存在下进行水解反应，能有效地得到产率极高的β-酮硫酯，而在 3.0 等量 NaOH 的存在下进行水解反应，则能成功地得到产率极高的β-酮酰胺。用这种绿色方法制备 β-keto thioesters 和 β-keto amides 可避免使用有害的有机溶剂、硫醇和硫代乙酸酯以及胺，这些物质可能会导致严重的环境和安全问题。Chem.2024, 20, 2225–2233. doi:10.3762/bjoc.20.190

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

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