Department of Chemistry, Xihua University, Chengdu 610039, China.
Asymmetric Synthesis and Chiral Technology Key Laboratory of Sichuan Province, Yibin 644000, China.
Molecules. 2022 Jul 22;27(15):4698. doi: 10.3390/molecules27154698.
Piperidine and pyrrolidine derivatives are important nitrogen heterocyclic structures with a wide range of biological activities. However, reported methods for their construction often face problems of requiring the use of expensive metal catalysts, highly toxic reaction reagents or hazardous reaction conditions. Herein, an efficient route from halogenated amides to piperidines and pyrrolidines was disclosed. In this method, amide activation, reduction of nitrile ions, and intramolecular nucleophilic substitution were integrated in a one-pot reaction. The reaction conditions were mild and no metal catalysts were used. The synthesis of a variety of N-substituted and some C-substituted piperidines and pyrrolidines became convenient, and good yields were obtained.
哌啶和吡咯烷衍生物是具有广泛生物活性的重要氮杂环结构。然而，报道的这些化合物的构建方法通常存在需要使用昂贵的金属催化剂、剧毒反应试剂或危险反应条件等问题。在此，本文揭示了一种从卤代酰胺到哌啶和吡咯烷的高效合成路线。在该方法中，酰胺的活化、腈离子的还原和分子内亲核取代在一锅反应中集成在一起。反应条件温和，无需使用金属催化剂。各种 N-取代和一些 C-取代的哌啶和吡咯烷的合成变得方便，并且获得了良好的收率。
