The first proline-catalyzed Friedlander annulation: Regioselective synthesis of 2-substituted quinoline derivatives

被引：39
作者：
Jiang, Biao [1 ]
Dong, Jia-jia [1 ]
Jin, Yun [1 ]
Du, Xiao-long [1 ]
Xu, Min [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 16期
关键词：
aldol reactions; quinoline; cyclization; proline;
D O I：
10.1002/ejoc.200800121
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first proline-catalyzed Friedlander annulation for the synthesis of 2-substituted 4-trifluoromethyl quinoline derivatives is described. Excellent re gio selectivity as well as good yields were shown in a variety of cases, and a tandem aldol-cyclization pathway might be involved. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码：2693 / 2696
页数：4
相关论文
共 50 条
  • [31] A Review on Domino Condensation/Cyclization Reactions for the Synthesis of 2-Substituted 1,3-Benzothiazole Derivatives
    Liu, Xing
    Dong, Zhi-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) : 408 - 419
  • [32] Synthesis of Stannyl-Substituted D-Glucal Derivatives via Palladium-Catalyzed Regioselective Hydrostannation and Their Synthetic Applications
    Shamim, Anwar
    Barbeiro, Criatiane S.
    Ali, Bakhat
    Stefani, Helio A.
    CHEMISTRYSELECT, 2016, 1 (18): : 5653 - 5659
  • [33] Synthesis of 2-Substituted Indoles by Pd-Catalyzed Reductive Cyclization of 1-Halo-2-nitrobenzene with Alkynes
    Lokolkar, Manjunath S.
    Mane, Pravin A.
    Dey, Sandip
    Bhanage, Bhalchandra M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (05)
  • [34] Efficient Friedlander Synthesis of Quinoline Derivatives from 2-Aminoarylketones and Carbonyl Compounds Mediated by Recyclable PEG-Supported Sulfonic Acid
    Zhang, Xiao-Liang
    Wang, Qiu-Ying
    Sheng, Shou-Ri
    Wang, Qing
    Liu, Xiao-Ling
    SYNTHETIC COMMUNICATIONS, 2009, 39 (18) : 3293 - 3304
  • [35] Reagent-controlled diastereoselective synthesis of (2S,3R)- and (2R,3R)-2,3-diaminobutanoic acid derivatives using proline-catalyzed α-hydrazination reaction
    Makino, Kazuishi
    Kubota, Sayaka
    Hara, Sousuke
    Sakaguchi, Masaru
    Hamajima, Akinari
    Hamada, Yasumasa
    TETRAHEDRON, 2009, 65 (45) : 9468 - 9473
  • [36] Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: the direct synthesis of C2-functionalized indoles
    Liu, Gang
    Xu, Guangyang
    Li, Jian
    Ding, Dong
    Sun, Jiangtao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (09) : 1387 - 1390
  • [37] Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols
    Sun, Zhou
    Xiang, Kuirong
    Tao, Hua
    Guo, Liqun
    Li, Ying
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (33) : 6133 - 6139
  • [38] Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO
    Chen, Yong-Xing
    Qian, Ling-Feng
    Zhang, Wei
    Han, Bing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) : 9330 - 9333
  • [39] A facile enantioselective synthesis of (S)-N-(5-chlorothiophene-2-sulfonyl)-β,β-diethylalaninol via proline-catalyzed asymmetric α-aminooxylation and α-amination of aldehyde
    Rawat, Varun
    Chouthaiwale, Pandurang V.
    Chavan, Vilas B.
    Suryavanshi, Gurunath
    Sudalai, Arumugam
    TETRAHEDRON LETTERS, 2010, 51 (50) : 6565 - 6567
  • [40] Synthesis of 2-substituted indoles by iridium (III)-catalyzed C-H functionalization of N-phenylpyridin-2-amines
    Zhang, Lei
    Chen, Junyu
    Chen, Jinkang
    Jin, Licheng
    Zheng, Xiangyun
    Jiang, Xinpeng
    Yu, Chuanming
    TETRAHEDRON LETTERS, 2019, 60 (15) : 1053 - 1056
12345