通过微波促进的三组分Kindler反应制备硫代酰胺结构单元。

Preparation of thioamide building blocks via microwave-promoted three-component kindler reactions.

作者信息

Zbruyev Oleksandr I, Stiasni Nikola, Kappe C Oliver

机构信息

Institute of Chemistry, Karl-Franzens-University Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

出版信息

J Comb Chem. 2003 Mar-Apr;5(2):145-8. doi: 10.1021/cc0200538.

DOI:10.1021/cc0200538

PMID:12625704

Abstract

A microwave-enhanced variation of the Kindler thioamide synthesis is introduced. Taking advantage of the sealed vessel capabilities of a dedicated single-mode microwave reacto,r a diverse selection of 13 aldehyde and 12 amine precursors was utilized in the construction of a representative 34-member library of substituted thioamides. The three-component condensations of aldehydes, amines, and elemental sulfur were carried out using 1-methyl-2-pyrrolidone (NMP) as solvent employing microwave flash heating at 110-180 degrees C for 2-20 min. A simple workup protocol allows the isolation of synthetically valuable primary, secondary, and tertiary thioamide building blocks in 83% average yield and >90% purity.

摘要

介绍了一种微波增强的Kindler硫代酰胺合成方法。利用专用单模微波反应器的密封容器功能，在构建一个具有代表性的34个成员的取代硫代酰胺库时，使用了多种选择的13种醛和12种胺前体。醛、胺和元素硫的三组分缩合反应以1-甲基-2-吡咯烷酮（NMP）为溶剂，在110-180℃下进行微波快速加热2-20分钟。一个简单的后处理方案能够以83%的平均产率和>90%的纯度分离出具有合成价值的伯、仲和叔硫代酰胺结构单元。