Radical cyclisation onto imidazoles and benzimidazoles

被引:51
作者
Aldabbagh, F [1 ]
Bowman, WR [1 ]
机构
[1] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England
关键词
D O I
10.1016/S0040-4020(99)00104-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New synthetic methodology has been developed for the synthesis of [1,2-a]Fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(omega-alkyl) radicals are generated using Bu3SnH from N-(omega-phenylselanyl)aIkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used as the leaving groups in the homolytic substitutions. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4109 / 4122
页数:14
相关论文
共 40 条
  • [1] Synthesis of heterocycles by radical cyclisation
    Aldabbagh, F
    Bowman, WR
    [J]. CONTEMPORARY ORGANIC SYNTHESIS, 1997, 4 (04): : 261 - 280
  • [2] Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH
    Aldabbagh, F
    Bowman, WR
    Mann, E
    [J]. TETRAHEDRON LETTERS, 1997, 38 (45) : 7937 - 7940
  • [3] Radical cyclisation onto imidazoles and benzimidazoles
    Aldabbagh, F
    Bowman, WR
    [J]. TETRAHEDRON LETTERS, 1997, 38 (21) : 3793 - 3794
  • [4] STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .39. SYNTHESIS OF BENZIMIDAZOLES CONTAINING A FUSED ALICYCLIC RING BY RHODIUM - CATALYZED HYDROFORMYLATION OF N-ALKENYL-1,2-DIAMINOBENZENES
    ANASTASIOU, D
    CAMPI, EM
    CHAOUK, H
    JACKSON, WR
    [J]. TETRAHEDRON, 1992, 48 (36) : 7467 - 7478
  • [5] SYNTHESIS OF 5H-PYRROLO[1,2-C]IMIDAZOLE AND 5H-PYRROLO[1,2-A]IMIDAZOLE
    ANTONINI, I
    FRANCHETTI, P
    GRIFANTINI, M
    MARTELLI, S
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (01) : 111 - 112
  • [6] OXIDATIVE RADICAL CYCLIZATION TO PYRROLES UNDER REDUCING CONDITIONS - REDUCTIVE DESULFONYLATION OF ALPHA-SULFONYLPYRROLES WITH TRI-N-BUTYLTIN HYDRIDE
    ANTONIO, Y
    DELACRUZ, ME
    GALEAZZI, E
    GUZMAN, A
    BRAY, BL
    GREENHOUSE, R
    KURZ, LJ
    LUSTIG, DA
    MADDOX, ML
    MUCHOWSKI, JM
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (01): : 15 - 22
  • [7] BECKWITH ALJ, 1995, J CHEM SOC CHEM COMM, P997
  • [8] IMIDAZOL-5-YL RADICALS AS REACTIVE INTERMEDIATES
    BOWMAN, WR
    TAYLOR, PF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04): : 919 - 924
  • [9] OXIDATION DURING REDUCTIVE CYCLIZATIONS USING BU3SNH
    BOWMAN, WR
    HEANEY, H
    JORDAN, BM
    [J]. TETRAHEDRON, 1991, 47 (48) : 10119 - 10128
  • [10] BOWMAN WR, 1995, TETRAHEDRON, V51, P11445