Utilizing Solubility Differences to Achieve Regiocontrol in the Synthesis of Substituted Quinoline-4-carboxylic Acids

被引：4
|
作者：
Lindsay-Scott, Peter J. [1 ]
Barlow, Helen [1 ]
机构：
[1] Eli Lilly & Co Ltd, Windlesham GU20 6PH, Surrey, England
来源：
SYNLETT | 2016年 / 27卷 / 10期
关键词：
heterocycles; quinolones; isatins; regioisomers; cyclization; GENERAL-METHOD; ISATINS; QUINOLINE; SEPARATION; MECHANISM;
D O I：
10.1055/s-0035-1561395
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A practical method for the regiocontrolled synthesis of substituted quinoline-4-carboxylic acids is described. Solubility differences between the product quinoline regioisomers enable their facile separation, thus avoiding any challenging chromatographic purifications and allowing access to highly substituted quinoline compounds in three steps from commercially available anilines.
引用
收藏
页码：1516 / 1520
页数：5
相关论文
共 50 条
  • [1] SYNTHESIS OF SUBSTITUTED QUINOLINE-4-CARBOXYLIC ACIDS
    LACKEY, K
    STERNBACH, DD
    SYNTHESIS-STUTTGART, 1993, (10): : 993 - 997
  • [2] On some substituted quinoline-4-carboxylic acid
    Benary, E
    BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1933, 66 : 1569 - 1571
  • [3] Synthesis, Characterization, and Antileishmanial Activity of Certain Quinoline-4-carboxylic Acids
    Abdelwahid, Mazin A. S.
    Elsaman, Tilal
    Mohamed, Malik S.
    Latif, Sara A.
    Mukhtar, Moawia M.
    Mohamed, Magdi A.
    JOURNAL OF CHEMISTRY, 2019, 2019
  • [4] Synthesis, Leishmanicidal and Enzyme Inhibitory Activities of Quinoline-4-Carboxylic Acids
    Khan, Khalid Mohammed
    Saied, Sumayya
    Mughal, Uzma Rasool
    Munawar, Marium
    Samreen
    Khan, Ajmal
    Perveen, Shahnaz
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2009, 31 (05): : 809 - 818
  • [5] Synthesis of spiropyrrolizidenes and 3-substituted quinoline-4-carboxylic acids from 7-bromoisatin
    Imanishimwe, Aphrodis
    Desrochers, Linda
    Goodwin, Thomas
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [6] Synthesis of the 4-substituted quinolines and of quinoline-4-carboxylic acid - (Quinoline group, I announcement)
    Thielepape, E
    BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1922, 55 : 127 - 135
  • [7] Quinoline-4-carboxylic acid
    Dobson, AJ
    Gerkin, RE
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 1883 - 1885
  • [8] Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation
    Hui Zhu~*
    Chinese Chemical Letters, 2010, 21 (01) : 35 - 38
  • [9] Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation
    Zhu, Hui
    Yang, Ri Fang
    Yun, Liu Hong
    Li, Jin
    CHINESE CHEMICAL LETTERS, 2010, 21 (01) : 35 - 38
  • [10] Synthesis and Monoamine Oxidase Inhibition Properties of (Sulfamoylphenyl)quinoline-4-carboxylic Acids
    Efimova, J.
    Shetnev, A.
    Korsakov, M.
    Petersen, E.
    Petzer, A.
    Petzer, J. P.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (10) : 2593 - 2602
12345