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Mild and highly efficient deacetylation of acetamido and acetoxy coumarins: A convenient and expeditious synthesis of substituted 3-aminocoumarins
Synthetic Communications ( IF 1.8 ) Pub Date : 2021-08-31 , DOI: 10.1080/00397911.2021.1968904
Jana Krajňáková 1 , Jakub Joniak 1 , Martin Putala 1 , Renáta Górová 2 , Helena Jurdáková 2 , Henrieta Stankovičová 1
Affiliation  

Abstract

A convenient protocol for efficient and cost-effective method for synthesis of substituted 3-aminocoumarins has been developed. The synthetic route involves expeditious and fast quantitative deacetylation of readily available acetamido derivative under anhydrous acidic conditions, employing thionyl chloride in methanol, without formation of undesired substituted 3-hydroxycoumarins. The method is suitable for derivatives bearing electron-donating as well as electron-withdrawing groups at position 7 of the coumarin scaffold. Under these conditions, a series of acetoxy substituted 3-dialkylaminocoumarins has been also successfully deacetylated to afford easily isolable corresponding hydroxy derivatives in high yields.



中文翻译:

乙酰氨基和乙酰氧基香豆素的温和高效脱乙酰化:一种方便快捷的取代 3-氨基香豆素合成

摘要

已开发出一种用于合成取代 3-氨基香豆素的高效且经济的方法的便捷方案。合成路线包括在无水酸性条件下使用亚硫酰氯在无水酸性条件下快速和快速定量脱乙酰化容易获得的乙酰胺衍生物,而不会形成不需要的取代的 3-羟基香豆素。该方法适用于香豆素支架第7位带有给电子和吸电子基团的衍生物。在这些条件下,一系列乙酰氧基取代的 3-二烷基氨基香豆素也已成功脱乙酰,以高产率提供易于分离的相应羟基衍生物。

更新日期:2021-11-03
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