Solid-phase synthesis of pyrazolines and isoxazolines with sodium benzenesulfinate as a traceless linker

被引:52
|
作者
Chen, Y [1 ]
Lam, YL [1 ]
Lai, YH [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
D O I
10.1021/ol0340888
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The preparation of pyrazoline and isoxazoline derivatives with traceless solid-phase sulfone linker strategy is described. Key steps involved in the solid-phase synthetic procedure include (i) sulfinate S-alkylation, (ii) sulfone anion alkylation, (iii) gamma-hydroxy sulfone --> gamma-ketosulfone oxidation, and (iv) traceless product release via elimination-cyclization. A library of 12 pyrazolines and isoxazolines was synthesized.
引用
收藏
页码:1067 / 1069
页数:3
相关论文
共 50 条
  • [21] Traceless solid-phase synthesis of carbolinones
    Chern, MS
    Shih, YK
    Dewang, PM
    Li, WR
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (06): : 855 - 858
  • [22] Traceless solid-phase α-hydroxytropolone synthesis
    D'Erasmo, Michael P.
    Masaoka, Takashi
    Wilson, Jennifer A.
    Hunte, Errol M., Jr.
    Beutler, John A.
    Le Grice, Stuart F. J.
    Murelli, Ryan P.
    MEDCHEMCOMM, 2016, 7 (09) : 1789 - 1792
  • [23] A solid-phase traceless synthesis of tetrahydroquinoxalines
    Krchnák, V
    Smith, J
    Vágner, J
    TETRAHEDRON LETTERS, 2001, 42 (13) : 2443 - 2446
  • [24] A traceless solid-phase synthesis of pteridines
    Gibson, CL
    La Rosa, S
    Suckling, CJ
    TETRAHEDRON LETTERS, 2003, 44 (06) : 1267 - 1270
  • [25] Traceless Solid-Phase Organic Synthesis
    Cankarova, Nadezda
    Schutznerova, Eva
    Krchnak, Viktor
    CHEMICAL REVIEWS, 2019, 119 (24) : 12089 - 12207
  • [26] Traceless solid-phase organic synthesis
    Blaney, P
    Grigg, R
    Sridharan, V
    CHEMICAL REVIEWS, 2002, 102 (07) : 2607 - 2624
  • [27] Traceless Solid-Phase Synthesis of Trifluoromethylarenes
    Doebele, Marion
    Wiehn, Matthias S.
    Braese, Stefan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11533 - 11535
  • [28] Solid-phase synthesis of 2-methoxyaniline derivatives by the traceless silicon linker strategy
    Curtet, S
    Langlois, M
    TETRAHEDRON LETTERS, 1999, 40 (49) : 8563 - 8566
  • [29] Traceless solid-phase synthesis of substituted benzimidazoles via a base-cleavable linker
    Tumelty, D
    Cao, K
    Holmes, CP
    ORGANIC LETTERS, 2001, 3 (01) : 83 - 86
  • [30] Studies on the solid-phase synthesis of cyclic peptides using arene chromium "traceless" linker.
    Rigby, JH
    Kondratenko, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U124 - U124