A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines
A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines
复制标题
DOI：
10.1021/jo070840x
复制
发表时间：
2007-08-03
影响因子：
3.6
通讯作者：
Orru, Romano V. A.
中科院分区：
文献类型：
--
作者：
Elders, Niels;Schmitz, Rob F.;Orru, Romano V. A.
用14种不同的溶剂研究了α-酸性异腈、伯胺和羰基化合物之间的多组分反应。根据所使用的异氰化物，在不同的溶剂中观察到三组分合成2 H-2-咪唑啉的最佳产率。溶剂可以按购买的形式使用，并且不需要亚胺的原位预形成。通过选择合适的溶剂，可以显著地扩大相容性异腈的范围，使其朝向α-酸性较低的异腈。通过在更高浓度下进行反应并避免通过柱色谱法纯化来实现进一步的工艺简化，从而为该三组分反应提供了快速、易于进行且资源高效的方案。
A multicomponent reaction between alpha-acidic isonitriles, primary amines, and carbonyl compounds was studied using 14 different solvents. Depending on the isocyanide that was used, optimal yields for the three-component synthesis of 2H-2-imidazolines were observed in different solvents. The solvents could be used as purchased, and in situ preformation of the imine was not required. By selecting the appropriate solvent, it was possible to considerably expand the range of compatible isocyanides toward less alpha-acidic isocyanides. Further process simplification was achieved by performing the reaction at higher concentrations and avoiding purification by column chromatography, resulting in a fast, easy to perform, and resource-efficient protocol for this three-component reaction.