An Acid-Catalysed Conversion of 2-(4-Quinazolinylamino)benzoic Acid into 2-(2-Aminophenyl)-4(1H)-Quinazolinone

被引:2
|
作者
Sneddon, Helen F. [1 ]
Lynn, Sean M. [1 ]
机构
[1] GlaxoSmithKline Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
rearrangement; tandem reaction; nucleophilic aromatic substitution; bicyclic compounds; fused ring systems;
D O I
10.1055/s-0030-1259540
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An acid-catalysed conversion of N-arylcarboxy-4-quinazolinones into 2-(2-aminoaryl)-4(1H)-quinazolinones has been observed. This reaction allows for a nucleophilic aromatic substitution reaction between aminobenzoic acids and 4-chloroquinazolines to form N-arylcarboxy-4-quinazolinones to be followed in situ by a conversion into 2-(2-aminoaryl)-4(1H)-quinazolinones in a one-pot tandem process.
引用
收藏
页码:573 / 575
页数:3
相关论文
共 50 条
  • [41] PHOTOLYSIS OF BENZOIC-ACID 2-(2,4,6-TRICHLOROPHENYL)HYDRAZIDE
    KOSHY, KT
    FRIEDMAN, AR
    VANDERSLIK, AL
    GRABER, DR
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1975, 23 (06) : 1084 - 1088
  • [42] Dehydration of 2-(4′-ethylbenzoyl) benzoic acid to 2-ethylanthraquinone over H-β zeolite impregnated with citric acid
    Zhai Lingjuan
    Liu Min
    Dong Xiangmie
    Song Chunshan
    Guo Xinwen
    CHINESE JOURNAL OF CATALYSIS, 2008, 29 (08) : 701 - 704
  • [43] Synthesis of 2-[2-(2-aminophenyl)ethyl]-6-R-quinnoline-4-carboxylic acids from 2-[2-(2-nitrophenyl)ethenyl]-6-R-quinoline-4-carboxylic Acids
    A. G. Kashaev
    A. V. Zimichev
    Yu. N. Klimochkin
    M. N. Zemtsova
    Russian Journal of Organic Chemistry, 2010, 46 : 1425 - 1426
  • [44] 2-(2-Hydroxy-4-methoxybenzoyl)benzoic acid derivatives of Group 4 metal alkoxides
    Boyle, Timothy J.
    Yonemoto, Daniel T.
    Neville, Michael L.
    Bingham, Samuel P.
    JOURNAL OF COORDINATION CHEMISTRY, 2014, 67 (05) : 747 - 765
  • [45] Synthesis of 2-[2-(2-aminophenyl)ethyl]-6-R-quinnoline-4-carboxylic acids from 2-[2-(2-nitrophenyl)ethenyl]-6-R-quinoline-4-carboxylic Acids
    Kashaev, A. G.
    Zimichev, A. V.
    Klimochkin, Yu N.
    Zemtsova, M. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (09) : 1425 - 1426
  • [46] Dehydration of 2-(4′-ethyl benzoyl) benzoic acid over H-beta modified with citric acid
    Xu, RS
    Guo, XW
    Wang, GR
    Liu, J
    Zhang, ZX
    CHINESE JOURNAL OF CATALYSIS, 2005, 26 (11) : 933 - 934
  • [47] Bronsted Acid Catalyzed Cascade Reactions of 2-[(2-Aminophenyl)ethynyl]phenylamine Derivatives with Aldehydes: A New Approach to the Synthesis of 2,2′-Disubstituted 1H,1′H-3,3′-Biindoles
    Arcadi, Antonio
    Chiarini, Marco
    D'Anniballe, Gaetano
    Marinelli, Fabio
    Pietropaolo, Emanuela
    ORGANIC LETTERS, 2014, 16 (06) : 1736 - 1739
  • [48] 2-(Benzotriazol-1-ylmethylamino)benzoic acid
    Wang, Yao
    Yin, Mai-Hua
    Zhang, Guo-Fang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O735 - U1609
  • [49] Synthesis of 2-(2-Aminophenyl)-4-arylquinazoline Derivatives by Reaction of 2-Aminoarylbenzimidamides with Isatoic Anhydride
    El-Shaieb, Kamal M.
    Jones, Peter G.
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2009, 64 (08): : 945 - 951
  • [50] Crystal and Molecular Structure of the 1:2 Salt Formed Between 1,2-(4-Pyridyl)Ethane and 2-(4-Hydroxyphenylazo)Benzoic Acid
    Corlette, Ellen M.
    Tiekink, Edward R. T.
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2009, 39 (08) : 603 - 606