L-Proline-catalyzed five-component domino reaction leading to multifunctionalized 1,2,3,4-tetrahydropyridines

被引:44
作者
Jiang, Huan-Feng [1 ]
Li, Jing-Hao [1 ]
Chen, Zheng-Wang [1 ]
机构
[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Peoples R China
基金
中国国家自然科学基金;
关键词
ACTIVE METHYLENE-COMPOUNDS; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; MANNICH REACTION; ACID; EFFICIENT; AMINES; TETRAHYDROPYRIDINES; DERIVATIVES;
D O I
10.1016/j.tet.2010.10.041
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Multifunctionalized 1,2,3,4-tetrahydropyridines are concisely synthesized in good yields via L-proline-catalyzed or L-proline/FeCl3-cocatalyzed one-pot multicomponent reactions (MCRs). The MCRs involve a domino hydroamination/prins reaction/Mannich-type reaction/intramolecular dehydration-cyclization process. The molecular structure of 5baa, one of multifunctionalized 1,2,3,4-tetrahydropyridines, was confirmed by single-crystal X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9721 / 9728
页数:8
相关论文
共 72 条
  • [1] Synthesis and x-ray structure of a 1,2,3,6-tetrahydropyridine-based phenylalanine mimetic
    Abell, AD
    Gardiner, J
    Phillips, AJ
    Robinson, WT
    [J]. TETRAHEDRON LETTERS, 1998, 39 (51) : 9563 - 9566
  • [2] Synthesis, crystal and antibacterial studies of diversely functionalized tetrahydropyridin-4-ol
    Aridoss, Gopalakrishnan
    Amirthaganesan, Shanmugasundaram
    Jeong, Yeon Tae
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (07) : 2242 - 2249
  • [3] Substituted 2-methylene-1,3-oxazolidines,-1,3-thiazolidines,-1,3-benzothiazines,-1,3-oxazines, and substituted imidazopyrimidinediones from Cl(CH2)nNCO and Cl(CH2)nNCS and active methylene compounds
    Basheer, Ahmad
    Rappoport, Zvi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26) : 9743 - 9750
  • [4] Modulating the reactivity of α-isocyanoacetates:: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones
    Bonne, Damien
    Dekhane, Mouloud
    Zhu, Jieping
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) : 2485 - 2488
  • [5] Enediynes as antitumor compounds: Synthesis of tetrahydropyridine derivatives
    Brana, MF
    Moran, M
    deVega, MJP
    PitaRomero, I
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04) : 1369 - 1374
  • [6] Passerini Three-Component Reaction of Alcohols under Catalytic Aerobic Oxidative Conditions
    Brioche, Julien
    Masson, Geraldine
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2010, 12 (07) : 1432 - 1435
  • [7] Recent developments in imino Diels-Alder reactions
    Buonora, P
    Olsen, JC
    Oh, T
    [J]. TETRAHEDRON, 2001, 57 (29) : 6099 - 6138
  • [8] Bronsted acid-promoted domino reactions: a novel one-pot three-component synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines
    Cao, Hua
    Jiang, Huan-Feng
    Qi, Chao-Rong
    Yao, Wen-Juan
    Chen, Huo-Ji
    [J]. TETRAHEDRON LETTERS, 2009, 50 (11) : 1209 - 1214
  • [9] Development, Scope and Mechanisms of Multicomponent Reactions of Asymmetric Electron-Deficient Alkynes with Amines and Formaldehyde
    Cao, Hua
    Wang, Xiujun
    Jiang, Huanfeng
    Zhu, Qiuhua
    Zhang, Min
    Liu, Haiyang
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (36) : 11623 - 11633
  • [10] Caplan JF, 2001, J CHEM SOC PERK T 1, P2217, DOI 10.1039/b105091p