K2CO3-accelerated amidation of carboxylic acids using α-oxo ketene-N,S-acetals as amine surrogates

被引：3

作者：

Yu, Haifeng ^{[1
]}

Zhang, Xue ^{[1
]}

Li, Liangliang ^{[1
]}

Luo, Hui ^{[1
]}

Che, Guangbo ^{[1
]}

机构：

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

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期

关键词：

C-H AMIDATION; KETENE DITHIOACETALS; COUPLING REAGENTS; AMIDE FORMATION; ANNULATION; N; S-ACETALS; ALDEHYDES; ACCESS;

D O I：

10.1039/d2qo01716d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient K2CO3-accelerated amidation of carboxylic acids with alpha-oxo ketene-N,S-acetals as amine surrogates is developed. The amidation of carboxylic acids is achieved in the presence of 10 mol% of K2CO3 using readily available (E)-4-(alkylamino)-4-(ethylthio)but-3-en-2-ones as amine surrogates. The method represents the first example of the synthetic utility of C-N bond cleavage of alpha-oxo ketene-N,S-acetals. A plausible mechanism is proposed on the basis of the detailed studies, in which the base plays the key role during the transformation.

引用

页码：686 / 698

页数：13

共 24 条

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