Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines

被引：12
|
作者：
Chang, Meng-Yang [1 ]
Lee, Ming-Fang [1 ]
Lee, Nien-Chia [1 ]
Huang, Yu-Ping [1 ]
Lin, Chung-Han [1 ]
机构：
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 05期
关键词：
N-Bromosuccinimide; Boron trifluoride etherate; Homokainoid; 1,2,4-Tetrasubstituted-1,2,5,6-tetrahydropyridine; SUBSTITUTED L-ARGININE; PIPECOLIC ACID; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; BF3-PROMOTED SYNTHESIS; THROMBIN INHIBITORS; AMIDE DERIVATIVES; PIPERIDINES; ALKALOIDS; NITRILE;
D O I：
10.1016/j.tetlet.2010.11.131
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6-tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF(3)-OEt(2))-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：588 / 591
页数：4
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