Palladium-Catalyzed Direct Benzylation of Xanthines

被引：26
作者：
Sahnoun, Sophian [1 ]
Messaoudi, Samir [1 ]
Brion, Jean-Daniel [1 ]
Alami, Mouad [1 ]
机构：
[1] Univ Paris 11, BioCIS, Chim Therapeut Lab, Fac Pharm,UMR 8076, F-92296 Chatenay Malabry, France
来源：
CHEMCATCHEM | 2011年 / 3卷 / 05期
关键词：
C-H activation; chemoselectivity; heterocycles; inhibitors; palladium; INTERMOLECULAR DIRECT ARYLATION; C-H BONDS; HETEROAROMATIC-COMPOUNDS; BREAST-CANCER; ARYL HALIDES; DIHYDROFOLATE-REDUCTASE; PNEUMOCYSTIS-CARINII; AROMATASE INHIBITORS; COUPLING REACTION; ALKYL FORMATES;
D O I：
10.1002/cctc.201000439
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
An efficient and versatile synthetic palladium-catalyzed sp(2) C-H bond activation approach for the preparation of a series of C8-benzyl xanthines has been developed using benzyl chlorides as coupling partners. The reactions take place rapidly in 1,4-dioxane and proceed in the presence of [PdCl2(MeCN)(2)]/P(o-tolyl)(3) as a catalyst system and Cs2CO3 as a base to afford good to excellent yields of the corresponding C8-benzylated xanthines of biological interest.
引用
收藏
页码：893 / 897
页数：5
相关论文
共 74 条
  • [1] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides
    Ackermann, Lutz
    [J]. CHEMICAL COMMUNICATIONS, 2010, 46 (27) : 4866 - 4877
  • [2] Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles
    Ackermann, Lutz
    Barfuesser, Sebastian
    Pospech, Jola
    [J]. ORGANIC LETTERS, 2010, 12 (04) : 724 - 726
  • [3] Regioselective Ruthenium-Catalyzed Direct Benzylations of Arenes through C-H Bond Cleavages
    Ackermann, Lutz
    Novak, Petr
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 4966 - 4969
  • [4] Ackermann L, 2009, MODERN ARYLATION METHODS, P311, DOI 10.1002/9783527627325.ch9
  • [5] Potent tetracyclic guanine inhibitors of PDE1 and PDE5 cyclic guanosine monophosphate phosphodiesterases with oral antihypertensive activity
    Ahn, HS
    Bercovici, A
    Boykow, G
    Bronnenkant, A
    Chackalamannil, S
    Chow, J
    Cleven, R
    Cook, J
    Czarniecki, M
    Domalski, C
    Fawzi, A
    Green, M
    Gundes, A
    Ho, G
    Laudicina, M
    Lindo, N
    Ma, K
    Manna, M
    McKittrick, B
    Mirzai, B
    Nechuta, T
    Neustadt, B
    Puchalski, C
    Pula, K
    Silverman, L
    Smith, E
    Stamford, A
    Tedesco, RP
    Tsai, HG
    Tulshian, D
    Vaccaro, H
    Watkins, RW
    Weng, XY
    Witkowski, JT
    Xia, Y
    Zhang, HT
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (14) : 2196 - 2210
  • [6] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
    Alberico, Dino
    Scott, Mark E.
    Lautens, Mark
    [J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
  • [7] A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction
    Audisio, Davide
    Messaoudi, Samir
    Peyrat, Jean-Francois
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. TETRAHEDRON LETTERS, 2007, 48 (39) : 6928 - 6932
  • [8] Assessing the chemical diversity of an hsp90 database
    Audisio, Davide
    Messaoudi, Samir
    Ijjaali, Ismail
    Dubus, Elodie
    Petitet, Francois
    Peyrat, Jean-Francois
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) : 2000 - 2009
  • [9] A Simple Synthesis of Functionalized 3-Bromocoumarins by a One-Pot Three-Component Reaction
    Audisio, Davide
    Messaoudi, Samir
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) : 1046 - 1051
  • [10] Iron-catalysed Negishi coupling of benzyl halides and phosphates
    Bedford, Robin B.
    Huwe, Michael
    Wilkinson, Mark C.
    [J]. CHEMICAL COMMUNICATIONS, 2009, (05) : 600 - 602
12345678