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
相关论文
共 34 条
  • [1] Enantioselective synthesis of trans-4-methylpipecolic acid
    Alegret, Carlos
    Santacana, Ferran
    Riera, Antoni
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) : 7688 - 7692
  • [2] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
    Amat, M
    Llor, N
    Hidalgo, J
    Escolano, C
    Bosch, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1919 - 1928
  • [3] ANDERSON PC, 1998, Patent No. 5807870
  • [4] An asymmetric dihydroxylation route to (2S,3S)-3-hydroxypipecolic acid
    Bodas, MS
    Kumar, P
    [J]. TETRAHEDRON LETTERS, 2004, 45 (46) : 8461 - 8463
  • [5] Synthesis of piperidines
    Buffat, MGP
    [J]. TETRAHEDRON, 2004, 60 (08) : 1701 - 1729
  • [6] ARGATROBAN, A SELECTIVE, POTENT THROMBIN INHIBITOR
    BUSH, LR
    [J]. CARDIOVASCULAR DRUG REVIEWS, 1991, 9 (03): : 247 - 263
  • [7] Broadening the Synthetic Scope of the Iron(III)-Catalyzed Aza-Prins Cyclization
    Carballo, Ruben M.
    Valdomir, Guillermo
    Purino, Martin
    Martin, Victor S.
    Padron, Juan I.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (12) : 2304 - 2313
  • [8] Synthesis of cis-3,4-diarylpiperidines and cis-3,4-diaryltetrahydropyrans
    Chang, Meng-Yang
    Lin, Chun-Yu
    Hung, Ching-Yi
    [J]. TETRAHEDRON, 2007, 63 (16) : 3312 - 3320
  • [9] New synthesis of cis-3,4-diaryl-1-tosylpyrrolidines
    Chang, Meng-Yang
    Pai, Chun-Li
    Lin, Chun-Yu
    [J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3641 - 3644
  • [10] Selectfluor-promoted fluorination of piperidinyl olefins
    Chang, Meng-Yang
    Lee, Nien-Chia
    Lee, Ming-Fang
    Huang, Yu-Ping
    Lin, Chung-Han
    [J]. TETRAHEDRON LETTERS, 2010, 51 (45) : 5900 - 5903
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