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

被引：0
|
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
收藏
页码：2225 / 2233
页数：9
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