Efficient C2 functionalisation of 2H-2-imidazolines

被引:28
作者
Bon, Robin S. [1 ]
Sprenkels, Nanda E. [1 ]
Koningstein, Manoe M. [1 ]
Schmitz, Rob F. [1 ]
de Kanter, Frans J. J. [1 ]
Doemling, Alexander [2 ]
Groen, Marinus B. [1 ]
Orru, Romano V. A. [1 ]
机构
[1] Vrije Univ Amsterdam, Dept Chem, NL-1081 HV Amsterdam, Netherlands
[2] Univ Pittsburgh, Pittsburgh, PA 15261 USA
关键词
D O I
10.1039/b713065a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Alkylation and oxidation of 2H-2-imidazolines, followed by regioselective deprotection, thionation and microwave-assisted Liebeskind-Srogl reaction, efficiently led to 2-aryl-2-imidazolines as new analogues of p53-hdm2 interaction inhibitors (Nutlins).
引用
收藏
页码:130 / 137
页数:8
相关论文
共 22 条
  • [1] Multicomponent synthesis of 2-imidazolines
    Bon, RS
    van Vliet, B
    Sprenkels, NE
    Schmitz, RF
    de Kanter, FJJ
    Stevens, CV
    Swart, M
    Bickelhaupt, FM
    Groen, MB
    Orru, RVA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) : 3542 - 3553
  • [2] Novel multicomponent reaction for the combinatorial synthesis of 2-imidazolines
    Bon, RS
    Hong, CG
    Bouma, MJ
    Schmitz, RF
    de Kanter, FJJ
    Lutz, M
    Spek, AL
    Orru, RVA
    [J]. ORGANIC LETTERS, 2003, 5 (20) : 3759 - 3762
  • [3] A convenient preparation of enantiomerically pure (+)-(1R,2R)-and (-)-(1S,2S)-1,2-diamino-1,2-diphenylethanes
    Braddock, D. Christopher
    Redmond, Joanna M.
    Hermitage, Stephen A.
    White, Andrew J. P.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) : 911 - 916
  • [4] THIONATION REACTIONS OF LAWESSON REAGENTS
    CAVA, MP
    LEVINSON, MI
    [J]. TETRAHEDRON, 1985, 41 (22) : 5061 - 5087
  • [5] Imidazoline binding sites and their ligands: An overview of the different chemical structures
    Dardonville, C
    Rozas, I
    [J]. MEDICINAL RESEARCH REVIEWS, 2004, 24 (05) : 639 - 661
  • [6] A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines
    Elders, Niels
    Schmitz, Rob F.
    de Kanter, Frans J. J.
    Ruijter, Eelco
    Groen, Marinus B.
    Orru, Romano V. A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) : 6135 - 6142
  • [7] NMR structure of a complex between MDM2 and a small molecule inhibitor
    Fry, DC
    Emerson, SD
    Palme, S
    Vu, BT
    Liu, CM
    Podlaski, F
    [J]. JOURNAL OF BIOMOLECULAR NMR, 2004, 30 (02) : 163 - 173
  • [8] Reactions of 1-methylbenzimidazole derivatives with m-chloroperoxybenzoic acid
    Kaiya, T
    Aoyama, S
    Kohda, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (06) : 625 - 630
  • [9] THIONO COMPOUNDS .5. PREPARATION AND OXIDATION OF SOME THIONO DERIVATIVES OF IMIDAZOLES
    KARKHANIS, DW
    FIELD, L
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1985, 22 (01): : 49 - 57
  • [10] Switchable catalysis: Modular synthesis of functionalized pyrimidinones via selective sulfide and halide cross-coupling chemistry
    Kusturin, C
    Liebeskind, LS
    Rahman, H
    Sample, K
    Schweitzer, B
    Srogl, J
    Neumann, WL
    [J]. ORGANIC LETTERS, 2003, 5 (23) : 4349 - 4352