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

被引：1

作者：

Yu, Haifeng ^{[1
]}

Zhang, Wanting ^{[1
]}

Cui, Xuejing ^{[1
]}

Liu, Zida ^{[1
]}

Zhang, Xifu ^{[1
]}

Zhao, Xiaobo ^{[1
]}

机构：

[1] Baicheng Normal Univ, Coll Chem, Baicheng 137000, Jilin, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷

关键词：

alpha-oxo ketene N; S-acetals; beta-keto amide; beta-keto thioester; dodecylbenzenesulfonic acid; hydrolysis; EFFICIENT SYNTHESIS; C-C; DIRECT ACCESS; DITHIOACETALS; 2-PYRIDONES; ODORLESS; INDOLES;

D O I：

10.3762/bjoc.20.190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An eco-friendly selective hydrolysis of chain a-oxo ketene N,S-acetals in water for the switchable synthesis of (3-keto thioesters and (3-keto amides is reported. In refluxing water, the hydrolysis reactions of a-oxo ketene N,S-acetals in the presence of 1.0 equiv of dodecylbenzenesulfonic acid effectively afforded (3-keto thioesters in excellent yield, while (3-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 (3-keto thioesters and (3-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.

引用

页码：2225 / 2233

页数：9

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