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

页码：588 / 591

页数：4

共 50 条

[31] Synthesis of 1,2,4-trisubstituted 2-imidazolin-5-ones
Sobha, TD
Shafi, PM
ASIAN JOURNAL OF CHEMISTRY, 1997, 9 (04) : 881 - 883
[32] Approaches to 3,4,5-substituted piperidines via 1,2,5,6-tetrahydropyridines prepared by ring-closing metathesis
Buffat, Maxime G. P.
Thomas, Eric J.
TETRAHEDRON, 2016, 72 (04) : 451 - 463
[33] Use of labile pyridinium salts in the synthesis of 1,2,3,6-tetrahydropyridines
Prokopenko, LI
Silin, AY
Chigareva, SM
Ramsh, SM
ZHURNAL OBSHCHEI KHIMII, 1997, 67 (07): : 1187 - 1190
[34] Stereocontrolled alkylation of chiral pyridinium salt toward a short enantioselective access to 2-alkyl- and 2,6-dialkyl-1,2,5,6-tetrahydropyridines
Guilloteau-Bertin, B
Compère, D
Gil, L
Marazano, C
Das, BC
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (08) : 1391 - 1399
[35] Antiproliferative activity of 2-alkyl-4-halopiperidines and 2-alkyl-4-halo-1,2,5,6-tetrahydropyridines in solid tumor cell lines
Leon, Leticia G.
Carballo, Ruben M.
Vega-Hernandez, Maria C.
Martin, Victor S.
Padron, Juan I.
Padron, Jose M.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (10) : 2681 - 2684
[36] Facile domino reactions in the statistically controlled product- and stereoselective synthesis of densely functionalized cis-1,4-cyclohexa-1,4-dienes and trans,trans-trisubstituted-1,2,5,6-tetrahydropyridines
Harikrishnan, Palani Sokkan
Rajesh, Stephen Michael
Perumal, Subbu
TETRAHEDRON LETTERS, 2012, 53 (30) : 3880 - 3884
[37] Construction of dihydropyrimidine skeleton using 1,2,4-trisubstituted-1,3-diaza-1,3-butadienes
Cho, Hidetsura
Nishimura, Yoshio
Yasui, Yoshizumi
Yamaguchi, Masahiko
TETRAHEDRON LETTERS, 2012, 53 (09) : 1177 - 1179
[38] SYNTHESIS OF 1,2,4-TRISUBSTITUTED IMIDAZOLES AND 1,3,5-TRISUBSTITUTED 1,2,4-TRIAZOLES
Baumgartner, Corinne
Braendli, Lukas
Diederich, Francois
HETEROCYCLES, 2008, 76 (01) : 401 - 428
[39] SYNTHESIS AND STRUCTURE OF A 1,2,5,6-TETRAHYDRO-1,2,5,6-TETRABOROCINE
KRAMER, A
PRITZKOW, H
SIEBERT, W
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (07): : 926 - 927
[40] Expedient synthesis of 3-substituted-1,2,3,6-tetrahydropyridines
Alcaraz, Lilian
de Neuville, Bertrand Coquebert
Lister, Andrew
Roberts, Bryan
TETRAHEDRON LETTERS, 2011, 52 (45) : 5940 - 5942

← 1 2 3 4 5 →