Novel solid-phase synthetic method for combinatorial generation of a 4-hydroxyquinolin-2(1H)-one-based library

被引:7
作者
Jeon, Moon-Kook
La, Hyun Ju
Ha, Deok-Chan
Gong, Young-Dae
机构
[1] Korea Res Inst Chem Technol, Taejon 305600, South Korea
[2] Korea Univ, Dept Chem, Seoul 151742, South Korea
关键词
combinatorial chemistry; solid-phase synthesis; quinolinone; Dieckmann condensation; cyclative cleavage;
D O I
10.1055/s-2007-980368
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Utilizing polymer-bound anthranilic acid derivatives, we were able to obtain 4-hydroxyquinolin-2(1H)-ones in 50-99% five- or six-step overall yields and 65-95% purities through the adaptation of a Dieckmann-type condensation reaction to a C-C bond-forming cyclative cleavage step. The reactions on solid phase were monitored by on-bead ATR-FTIR spectroscopic methods, colorimetric tests, and/or cleavage experiments.
引用
收藏
页码:1431 / 1435
页数:5
相关论文
共 35 条
  • [1] Solid-phase combinatorial synthesis of 4-hydroxyquinolin-2(1H)-ones
    Sim, MM
    Lee, CL
    Ganesan, A
    TETRAHEDRON LETTERS, 1998, 39 (35) : 6399 - 6402
  • [2] A solid-phase synthetic method for 3,4-dihydro-1H-2,1-benzothiazin-4-one 2,2-dioxide derivatives
    Jeon, Moon-Kook
    Kim, Myung-Su
    Kwon, Jeong-Jin
    Gong, Young-Dae
    Lee, Duck-Hyung
    TETRAHEDRON, 2008, 64 (38) : 9060 - 9072
  • [3] A method of orthogonal oligosaccharide synthesis leading to a combinatorial library based on stationary solid-phase reaction
    Ako, Takuro
    Daikoku, Shusaku
    Ohtsuka, Isao
    Kato, Rumiko
    Kanie, Osamu
    CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (06) : 798 - 813
  • [4] A novel solid-phase synthetic method for 1,4-benzodiazepine-2,5-dione derivatives
    Jeon, Moon-Kook
    Kwon, Jeong-Jin
    Kim, Myung-Su
    Gong, Young-Dae
    SYNLETT, 2008, (11) : 1651 - 1656
  • [5] Novel solid-phase synthesis of 1,5-benzothiazepine-4-one derivatives
    Morton, GC
    Salvino, JM
    Labaudinière, RF
    Herpin, TF
    TETRAHEDRON LETTERS, 2000, 41 (17) : 3029 - 3033
  • [6] Novel Approaches for the Solid-Phase Synthesis of Dihydroquinazoline-2(1H)-One Derivatives and Biological Evaluation as Potential Anticancer Agents
    Wang, Qiong
    Pan, Ying
    Luo, Hongjun
    Zhang, Yanmei
    Gao, Fenfei
    Wang, Jinzhi
    Zheng, Jinhong
    MOLECULES, 2022, 27 (23):
  • [7] Solid-phase combinatorial synthesis of 1,4-benzoxazin-3(4H)-one and 1,4-benzothiazin-3(4H)-one derivatives
    Lee, CL
    Chan, KP
    Lam, YL
    Lee, SY
    TETRAHEDRON LETTERS, 2001, 42 (06) : 1167 - 1169
  • [8] 2-Phenylsubstituted-3-Hydroxyquinolin-4(1H)-one-Carboxamides: Structure-Cytotoxic Activity Relationship Study
    Soural, Miroslav
    Hlavac, Jan
    Funk, Petr
    Dzubak, Petr
    Hajduch, Marian
    ACS COMBINATORIAL SCIENCE, 2011, 13 (01) : 39 - 44
  • [9] Solid-phase synthesis of 3,4-dihydro-2(1H)-quinazolinones and 3,4-dihydro-1H-quinazolin-2-thiones
    Sun, Q
    Zhou, XM
    Kyle, DJ
    TETRAHEDRON LETTERS, 2001, 42 (25) : 4119 - 4121
  • [10] A Facile Solid Phase Synthesis of 2-Alkylthio-4(1H)-quinolones
    唐靖
    吴明光
    黄宪
    ChineseJournalofChemistry, 2003, (05) : 585 - 587