化学
亲核细胞
酰化
酰胺
吡啶
组合化学
有机化学
药物化学
催化作用
作者
Atsushi Umehara,Soma Shimizu,Makoto Sasaki
出处
期刊:Chemcatchem
[Wiley]
日期:2023-02-02
卷期号:15 (5)
被引量:4
标识
DOI:10.1002/cctc.202201596
摘要
Abstract In contrast to the considerable progress in the development of methodologies for amide bond formation in amines, the development of direct N ‐acylation of less nucleophilic N ‐heterocycles and amides with carboxylic acids is still challenging. In this report, we describe the direct N ‐acylation of less nucleophilic heterocycles and amides with carboxylic acids promoted by the 4‐( N , N ‐dimethylamino)pyridine N ‐oxide (DMAPO)/di‐ tert ‐butyl dicarbonate (Boc 2 O) system. The new one‐pot method, which does not involve pre‐activation of substrates, enables the direct N ‐acylation of a wide variety of nitrogen nucleophiles such as indole, carbazole, pyrrole, pyrazole, lactam, oxazolidinone, and anilide with carboxylic acids in high yield. The new method also exhibits excellent functional group tolerance and broad substrate scope. As the present method is practical, operationally simple, and scalable, it should find wide applications in both academic and industrial laboratories.
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