Efficient amidation of weak amines: synthesis, chiral separation by SFC, and antimicrobial activity of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) carboxamide,Organic & Biomolecular Chemistry

当前位置： X-MOL 学术 › Org. Biomol. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Efficient amidation of weak amines: synthesis, chiral separation by SFC, and antimicrobial activity of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) carboxamide
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2023-12-06 , DOI: 10.1039/d3ob01774e
Kathiravan Asokan _{1,

2,

3} , A Zahir Hussain ₂ , Andivelu Ilangovan ₃

Affiliation

An effective and straightforward method for the synthesis of 1-aminoanthracene-9,10-dione carboxamides by coupling a weakly reactive amine, 1-aminoanthracene-9,10-dione, and sterically hindered carboxylic acids was achieved using COMU as the coupling agent. Furthermore, making use of the advantages associated with the super-critical fluid chromatography (SFC) technique, a simplified and straightforward method for the chiral separation of optically active amide derivatives from the impurities associated with the reaction mixture, in a single step, was demonstrated. The antimicrobial activity of selected 1-aminoanthracene-9,10-dione carboxamides was studied. Advanced NMR and other spectral techniques were used for the thorough characterization of all the compounds. This study provides a general and simplified method for coupling a weak amine with a sterically hindered acid using COMU as a coupling agent, and demonstrates the separation of optically pure compounds from reaction related impurities in a single step using SFC, and identification of amide derivatives of 1-aminoanthracene-9,10-dione as potential antimicrobial agents.

中文翻译：

弱胺的高效酰胺化：N-(9,10-二氧代-9,10-二氢蒽-1-基)甲酰胺的合成、SFC手性分离以及抗菌活性

使用 COMU 作为偶联剂，通过偶联弱反应性胺、1-氨基蒽-9,10-二酮和位阻羧酸，实现了一种有效且简单的合成 1-氨基蒽-9,10-二酮甲酰胺的方法。此外，利用超临界流体色谱（SFC）技术的优势，证明了一种简单而直接的方法，可以在一个步骤中从反应混合物中的杂质中手性分离光学活性酰胺衍生物。。研究了选定的 1-氨基蒽-9,10-二酮甲酰胺的抗菌活性。使用先进的核磁共振和其他光谱技术对所有化合物进行彻底的表征。本研究提供了一种使用 COMU 作为偶联剂将弱胺与位阻酸偶联的通用且简化的方法，并演示了使用 SFC 在一步中将光学纯化合物与反应相关杂质分离，并鉴定了1-氨基蒽-9,10-二酮作为潜在的抗菌剂。

更新日期：2023-12-08

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南