A Practical Approach for the Transamidation of N,N-Dimethyl Amides with Primary Amines Promoted by Sodium tert-Butoxide under Solvent-Free Conditions,Synthesis

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A Practical Approach for the Transamidation of N,N-Dimethyl Amides with Primary Amines Promoted by Sodium tert-Butoxide under Solvent-Free Conditions
Synthesis ( IF 2.2 ) Pub Date : 2020-09-08 , DOI: 10.1055/s-0040-1705892
Hua Cheng ₁ , Cheng Chen ₂ , Rui Zhang ₁ , Jun-Chao Zhang ₁ , Wei-Yi Zhang ₁ , Yu-Qing He ₁ , Yu-Cheng Gu ₃

Affiliation

This paper is dedicated to Professor Youyou Tu, the 2015 Nobel Prize Laureate of Physiology or Medicine, on the occasion of her 90^th birthday

Abstract

A practical sodium tert-butoxide (NaOtBu)-mediated protocol is disclosed for the transamidation of various N,N-dimethyl amides with primary amines to afford the corresponding amides in moderate to good yields at room temperature under solvent-free conditions. This protocol features a facile work-up procedure and good functional group compatibility, especially for N,N-dimethyl amides with long-chain alkyl groups and heteroatom-containing amines. Notably, a few representative gram-scale reactions proceed smoothly to furnish the desired amides in high yields, which demonstrates the potential of this process for further practical applications. Several control experiments are carried out and a plausible mechanism is provided.

Publication History

Received: 29 May 2020

Accepted after revision: 22 July 2020

Publication Date:
08 September 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

无溶剂条件下叔丁醇钠促进的N，N-二甲酰胺与伯胺的氨基转移的实用方法

本文是专门为优优杜教授，生理学或医学诺贝尔奖2015年奖得主，在她90之际^个生日

抽象

公开了一种实用的叔丁醇钠（NaO t Bu）介导的方案，用于各种N，N-二甲基酰胺与伯胺的氨基转移，以在室温下在无溶剂条件下以中等至良好的收率得到相应的酰胺。该协议具有简便的后处理程序和良好的功能组兼容性，尤其适用于N，N具有长链烷基的-二甲基酰胺和含杂原子的胺。值得注意的是，一些代表性的克级反应可以顺利进行，以高收率提供所需的酰胺，这证明了该方法在进一步实际应用中的潜力。进行了几个控制实验，并提供了一个合理的机制。