Solid phase heterocyclic chemistry

被引:249
作者
Krchnak, V [1 ]
Holladay, MW [1 ]
机构
[1] ChemRx Adv Technol Inc, Tucson, AZ 85747 USA
关键词
D O I
10.1021/cr010123h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review is given of the methods for the traceless solid-phase synthesis of various heterocyclic compounds, whereby the presence of obvious traces of linkage to the solid support are eliminated. These approaches are organized into several distinct categories as follows: i) use of C-H linkers results in formation of a C-H bond in the seceding molecule during the cleavage step, ii) use of N-H linkers results in formation of an N-H bond in seceding molecule, iii) application of a cyclative cleavage strategy yields a newly formed C-N bond, and iiii) inducement of modifications to the target molecule during or after the cleavage step obscures or obliterates the previous point of attachment to the solid support.
引用
收藏
页码:61 / 91
页数:31
相关论文
共 153 条
  • [51] Gmeiner P, 1996, SYNTHESIS-STUTTGART, P1196
  • [52] Solid supported high-throughput organic synthesis of peptide β-turn mimetics via Petasis reaction/diketopiperazine formation
    Golebiowski, A
    Klopfenstein, SR
    Chen, JJ
    Shao, X
    [J]. TETRAHEDRON LETTERS, 2000, 41 (25) : 4841 - 4844
  • [53] REDUCTIVE ALKYLATION ON A SOLID-PHASE - SYNTHESIS OF A PIPERAZINEDIONE COMBINATORIAL LIBRARY
    GORDON, DW
    STEELE, J
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (01) : 47 - 50
  • [54] Solid phase synthesis of chiral 3-substituted quinazoline-2,4-diones
    Gouilleux, L
    Fehrentz, JA
    Winternitz, F
    Martinez, J
    [J]. TETRAHEDRON LETTERS, 1996, 37 (39) : 7031 - 7034
  • [55] ''Traceless'' solid-phase synthesis of furans via 1,3-dipolar cycloaddition reactions of isomunchnones
    Gowravaram, MR
    Gallop, MA
    [J]. TETRAHEDRON LETTERS, 1997, 38 (40) : 6973 - 6976
  • [56] Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handle
    Guillaumie, F
    Kappel, JC
    Kelly, NM
    Barany, G
    Jensen, KJ
    [J]. TETRAHEDRON LETTERS, 2000, 41 (32) : 6131 - 6135
  • [57] Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry
    Guillier, F
    Orain, D
    Bradley, M
    [J]. CHEMICAL REVIEWS, 2000, 100 (06) : 2091 - 2157
  • [58] Alkylidenation of esters on solid support and traceless synthesis of 2-substituted benzofurans
    Guthrie, EJ
    Macritchie, J
    Hartley, RC
    [J]. TETRAHEDRON LETTERS, 2000, 41 (25) : 4987 - 4990
  • [59] Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylic acids from malonic acid resin
    Hamper, BC
    Gan, KZ
    Owen, TJ
    [J]. TETRAHEDRON LETTERS, 1999, 40 (27) : 4973 - 4976
  • [60] Solid-phase synthesis of acyclic and cyclic amino acid derived urea peptidomimetics using phoxime resin
    Hamuro, Y
    Marshall, WJ
    Scialdone, MA
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (02): : 163 - 172