A One-Pot Dearomative Approach to C4-Alkylated Tetrahydropyridines and Tetrahydroquinolines
A One-Pot Dearomative Approach to C4-Alkylated Tetrahydropyridines and Tetrahydroquinolines
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DOI：
10.1002/ajoc.202000337
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发表时间：
2020-07-28
影响因子：
2.7
通讯作者：
Wang, Dong
中科院分区：
文献类型：
--
作者：
Dong, Linru;Ma, Xinyue;Wang, Dong
以吡啶和喹啉为原料，采用区域选择性一锅法合成了C4烷基化四氢吡啶和四氢喹啉。这种转变是由BF 3实现的。OEt 2-介导的，C4-选择性添加的格氏试剂，然后通过级联的烯胺质子化和随后的Et 3SiH还原所得的亚胺离子。该方法不仅为C4取代的THP和THQ的合成提供了一条简便的途径，而且为杂芳烃的脱芳提供了一种新的策略。
A regioselective one-pot approach to the synthesis of C4-alkylated tetrahydropyridines (THPs) and tetrahydroquinolines (THQs) by dearomatization of pyridines and quinolines has been developed. The transformation is achieved by the BF3 . OEt2-mediated, C4-selective addition of Grignard reagents, followed by a cascade of enamine protonation and the subsequent Et3SiH reduction of the resulting iminium ions. This protocol not only provides a facile synthetic approach to C4-substituted THPs and THQs, but also offers a new strategy for the dearomatization of heteroaromatics.