One-pot highly efficient synthesis of substituted pyrroles and N-bridgehead pyrroles by zinc-catalyzed multicomponent reaction
One-pot highly efficient synthesis of substituted pyrroles and N-bridgehead pyrroles by zinc-catalyzed multicomponent reaction
复制标题
锌催化多组分反应一锅高效合成取代吡咯和N-桥头吡咯
DOI：
10.1039/c003885g
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发表时间：
2010-01-01
影响因子：
3.2
通讯作者：
Zhan, Zhuang-ping
中科院分区：
文献类型：
--
作者：
Liu, Xiao-tao;Hao, Lu;Zhan, Zhuang-ping
一个方便的氯化锌（II）催化的区域选择性炔丙基化/胺化/环异构化过程已被开发用于合成取代的吡咯衍生物从炔丙基乙酸酯，烯氧基硅烷和伯胺。各种芳族和脂族炔丙基乙酸酯很好地参与反应，以良好的产率提供炔丙基化/胺化/环异构化产物，具有完全的区域选择性。一锅多组分偶联反应避免了中间体的分离，以高产率合成取代吡咯。氯化锌（II）作为一种多功能催化剂，在一锅中催化三种不同的机械过程。该方案已扩展到含多环片段的N-桥头吡咯的合成。
A convenient zinc(II) chloride-catalyzed regioselective propargylation/amination/cycloisomerization process has been developed for the synthesis of substituted pyrrole derivatives from propargylic acetates, enoxysilanes and primary amines. Various aromatic and aliphatic propargylic acetates participate well in the reaction, providing the propargylation/amination/cycloisomerization products in good yields with complete regioselectivity. The one-pot multicomponent coupling reaction furnishes substituted pyrroles in high yields by circumventing the intermediates' isolation. Zinc( II) chloride acts as a multifunctional catalyst and catalyzes three mechanistically distinct processes in a single-pot. The protocol developed has been extended to the synthesis of N-bridgehead pyrroles containing polycyclic fragments.