Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids

被引：8
|
作者：
Hermecz, I [1 ]
Vasvari-Debreczy, L [1 ]
Podanyi, B [1 ]
Kereszturi, G [1 ]
Balogh, M [1 ]
Horvath, A [1 ]
Varkonyi, P [1 ]
机构：
[1] Chinoin Chem & Pharmaceut Works Ltd, H-1325 Budapest, Hungary
来源：
HETEROCYCLES | 1998年 / 48卷 / 06期
关键词：
D O I：
10.3987/COM-98-8143
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).
引用
收藏
页码：1111 / 1116
页数：6
相关论文
共 50 条
  • [1] Synthesis of 1-substituted 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids as potential antimicrobial drugs
    Glushkov R.G.
    Marchenko N.B.
    Levshin I.B.
    Pharmaceutical Chemistry Journal, 1997, 31 (5) : 240 - 242
  • [2] 1-ethyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Lou, Benyong
    Bostrom, Dan
    Velaga, Sitaram P.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4281 - U3023
  • [3] 1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Li, Tao
    Tang, Li-Rong
    Zeng, Qiao-Ling
    Chen, Wei-Jin
    Huang, Biao
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2053 - U4652
  • [4] 1-Cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Li, XW
    Zhi, F
    Shen, JH
    Hu, YQ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2235 - O2236
  • [5] Synthesis and amination of 1-alkyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acids
    Glushkov R.G.
    Marchanko N.B.
    Levshin I.B.
    Dronova L.N.
    Pharmaceutical Chemistry Journal, 1997, 31 (5) : 267 - 271
  • [6] A NEW EFFICIENT ROUTE TO 4-OXO-1,4-DIHYDROQUINOLINE-2-CARBOXYLIC ESTERS
    COLTMAN, SCW
    EYLEY, SC
    RAPHAEL, RA
    SYNTHESIS-STUTTGART, 1984, (02): : 150 - 152
  • [7] 4-Oxo-1,4-dihydroquinoline-3-carboxamide Derivatives as New Axl Kinase Inhibitors
    Tan, Li
    Zhang, Zhang
    Gao, Dongylin
    Luo, Jinfeng
    Tu, Zheng-Chao
    Li, Zhengqiu
    Peng, Lijie
    Ren, Xiaomei
    Ding, Ke
    JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (14) : 6807 - 6825
  • [8] Regioselective Synthesis of 1-Substituted Indazole-3-carboxylic Acids
    Veerareddy, Arava
    Gogireddy, Surendrareddy
    Dubey, P. K.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) : 1311 - 1321
  • [9] 7-(3-Chlorophenylamino)-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid
    Al-Hiari, Yusuf Mohammad
    Qandil, Amjad M.
    Al-Zoubi, Rufaida M.
    Alzweiri, Muhammed H.
    Darwish, Rula M.
    Shattat, Ghassan F.
    Al-Qirim, Tariq M.
    MOLBANK, 2010, (02) : 1 - 3
  • [10] Synthesis and evaluation of antitrypanosomal activity of some thiosemicarbazide derivatives of 1-butyl-6-fluoro-7-morpholino-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
    Pyrih, Andriy
    Berninger, Michael
    Gzella, Andrzej
    Lesyk, Roman
    Holzgrabe, Ulrike
    SYNTHETIC COMMUNICATIONS, 2018, 48 (14) : 1883 - 1891
12345