Synthesis of fluorine-containing 2-(1-aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic acids

被引:0
|
作者
Fokin, A. S. [1 ]
Burgart, Ya. V. [1 ]
Saloutin, V. I. [1 ]
Chupakhin, O. N. [1 ]
机构
[1] Russian Acad Sci, Inst Organ Synth, Ural Div, Ekaterinburg 620219, Russia
基金
俄罗斯基础研究基金会;
关键词
Hydrolysis; Ethyl; Organic Chemistry; Toluene; Dehydration;
D O I
10.1007/s11178-005-0349-x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acid hydrolysis of ethyl 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetates gives 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3-yl)-2,2-dihydroxyacetic acids which undergo dehydration on heating in toluene to afford 2-(1-aryl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydrocinnolin-3yl)-2-oxoacetic acids. Reactions of the latter with excess morpholine result in replacement of two fluorine atoms in positions 5 and 7 by the amine residues.
引用
收藏
页码:1374 / 1376
页数:3
相关论文
共 50 条
  • [1] Synthesis of Fluorine-Containing 2-(1-Aryl-4-oxo-1,4-dihydrocinnolin-3-yl)-2-oxoacetic Acids
    A. S. Fokin
    Ya. V. Burgart
    V. I. Saloutin
    O. N. Chupakhin
    Russian Journal of Organic Chemistry, 2005, 41 : 1374 - 1376
  • [2] A novel method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid
    Pan, Xianhua
    Lu, Qingling
    Li, Xiaojun
    Zhang, Jianshui
    Yu, Wansheng
    Liu, Feng
    JOURNAL OF CHEMICAL RESEARCH, 2013, (12) : 722 - 723
  • [3] Theoretical Study and Experimental Analysis on 2-(1-Ethyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-2-oxoacetic Acid (3) Using the DFT Approach
    Shimaa Abdel Halim
    Journal of Solution Chemistry, 2018, 47 : 172 - 197
  • [4] Theoretical Study and Experimental Analysis on 2-(1-Ethyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-2-oxoacetic Acid (3) Using the DFT Approach
    Halim, Shimaa Abdel
    JOURNAL OF SOLUTION CHEMISTRY, 2018, 47 (01) : 172 - 197
  • [5] Structure, conformations, vibrations and quantum chemical investigations of 2-(1H-indol-3-yl)-2-oxoacetic acid
    Arjunan, V.
    Durga Devi, G.
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1256
  • [6] A facile method for the synthesis of 2-(3-hydroxy-1-adamantyl)-2-oxoacetic acid and it's optimization
    Wang, Hui-fei
    Gan, Run
    Zhou, Jing
    Liao, Qi
    Wang, Tian-bao
    Zhong, Cai-ling
    Xiang, Yuan-yuan
    Lin, Hong-bo
    Hu, Xiang-nan
    PAKISTAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2018, 31 (04) : 1393 - 1397
  • [7] SYNTHESIS AND PROPERTIES OF 2-SUBSTITUTED 1-ARYL-4-OXO-1,4-DYHYDROPYRIDO[2,3-D]PYRIMIDINES
    DEMINA, LM
    GAVRILOV, MY
    VAHRIN, MJ
    KONSHIN, ME
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1991, (10): : 1397 - 1401
  • [8] An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
    Liao, Qi
    Jiang, Lan
    Li, Cong
    Shen, Yaling
    Wang, Min
    Cao, Chengkun
    Hu, Xiangnan
    JOURNAL OF CHEMISTRY, 2019, 2019
  • [9] Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide
    Gupta, G
    Wagh, SB
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2006, 45 (03): : 697 - 702
  • [10] Synthesis of new (3,4-dihydro-3-oxo-2H-1,4-benzoxazin-2-yl)-N-( 4-aryl-3-chloro-2-oxo-azetidin-1-yl) acetamides
    Jayamma, Y
    Patnaik, S
    Kalyane, N
    Reddy, VM
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2003, 12 (04) : 351 - 354