开发一种基于三嗪二酮的脱水缩合试剂，其中含有 4-（二甲基氨基）吡啶作为酰基转移催化剂。

Development of a triazinedione-based dehydrative condensing reagent containing 4-(dimethylamino)pyridine as an acyl transfer catalyst.

机构信息

Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

Faculty of Pharmaceutical Sciences, Matsuyama University, 4-2, Bunkyo-cho, Matsuyama 790-8578, Japan.

出版信息

Org Biomol Chem. 2021 Jun 2;19(21):4712-4719. doi: 10.1039/d1ob00450f.

DOI:10.1039/d1ob00450f

PMID:33969372

Abstract

A new triazinedione-based reagent, (N,N'-dialkyl)triazinedione-4-(dimethylamino)pyridine (ATD-DMAP) was developed for the operationally simple dehydrative condensation of carboxylic acids. This reagent comprises an ATD core and DMAP as the leaving group, which is liberated into the reaction system to accelerate acyl transfer reactions. Upon adding ATD-DMAP to a mixture of carboxylic acids and alcohols in the presence of an amine base, the corresponding esters were formed rapidly at room temperature. Moreover, dehydrative condensation between carboxylic acids and amines using ATD-DMAP proceeded in high yield.

摘要

一种新的三嗪二酮基试剂，（N，N'-二烷基）三嗪二酮-4-（二甲基氨基）吡啶（ATD-DMAP），被开发用于羧酸的操作简单的脱水缩合反应。该试剂包含 ATD 核和 DMAP 作为离去基团，在反应体系中释放出来以加速酰基转移反应。当在胺碱的存在下将 ATD-DMAP 添加到羧酸和醇的混合物中时，相应的酯在室温下迅速形成。此外，使用 ATD-DMAP 进行羧酸和胺之间的脱水缩合反应以高产率进行。