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 30 条
  • [1] [Anonymous], CHEM HETEROCYCLIC 1
  • [2] BOWERS A, 1954, J CHEM SOC, P2458
  • [3] BUNIN BA, 1998, COMBINATORIAL INDEX, P9
  • [4] Solid-phase synthesis of isoxazolines
    Chandrasekhar, S
    Raza, A
    Reddy, MV
    Yadav, JS
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (06): : 652 - 655
  • [5] Solid-phase synthesis of imidazo[1,2-a]pyridine using sodium benzenesulfinate as a traceless linker
    Chen, Y
    Lam, YL
    Lai, YH
    [J]. ORGANIC LETTERS, 2002, 4 (22) : 3935 - 3937
  • [6] Solid phase synthesis of pyridazine derivatives using polymer-bound sodium benzenesulfinate
    Chen, Y
    Lam, YL
    Lee, SY
    [J]. CHEMISTRY LETTERS, 2001, (03) : 274 - 275
  • [7] Solid-phase synthesis of Δ2-isoxazolines
    Cheng, JF
    Mjalli, AMM
    [J]. TETRAHEDRON LETTERS, 1998, 39 (09) : 939 - 942
  • [8] The sulfone linker in solid-phase synthesis: Preparation of 3,5-disubstituted cyclopent-2-enones
    Cheng, WC
    Kurth, MJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) : 4387 - 4391
  • [9] Solid-phase synthesis of novel isoxazolocyclobutanones and isoxazolinocyclobutenones
    Cheng, WC
    Wong, M
    Olmstead, MM
    Kurth, MJ
    [J]. ORGANIC LETTERS, 2002, 4 (05) : 741 - 744
  • [10] Dimsyl anion in the monoalkylation of solid-phase alkyl sulfones
    Cheng, WC
    Lin, CC
    Kurth, MJ
    [J]. TETRAHEDRON LETTERS, 2002, 43 (16) : 2967 - 2970