Pd-Catalyzed Reaction of Sterically Hindered Hydrazones with Aryl Halides: Synthesis of Tetra-Substituted Olefins Related to iso-Combretastatin A4

被引:110
作者
Brachet, Etienne [1 ]
Hamze, Abdallah [1 ]
Peyrat, Jean-Francois [1 ]
Brion, Jean-Daniel [1 ]
Alami, Mouad [1 ]
机构
[1] Univ Paris 11, CNRS, Chim Therapeut Lab, Fac Pharm,BioCIS UMR 8076, F-92296 Chatenay Malabry, France
关键词
CROSS-COUPLING REACTIONS; ANTITUMOR-ACTIVITY; ANTINEOPLASTIC AGENTS; A-4; ANALOGS; TUBULIN; POTENT; 1,1-DIARYLETHYLENES; INHIBITORS; CHEMISTRY;
D O I
10.1021/ol101639g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PdCl(2)(MeCN)(2) in combination with dppp proved to be a powerful and efficient catalyst for the coupling of sterically hindered N-arylsulfonylhydrazones with aryl halides, thus providing a flexible and convergent access to tetrasubstituted olefins related to iso-combretastatin A4 in good yields. This new protocol has been applied successfully to the formal synthesis of biphenylisopropylidene 4-pyridine CYP17 inhibitor, 12b, of biological interest.
引用
收藏
页码:4042 / 4045
页数:4
相关论文
共 28 条
  • [1] THE DECOMPOSITION OF TOLUENE-PARA-SULPHONYLHYDRAZONES BY ALKALI
    BAMFORD, WR
    STEVENS, TS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1952, (DEC): : 4735 - 4740
  • [2] Pd-catalyzed cross-coupling reactions with carbonyls:: Application in a very efficient synthesis of 4-aryltetrahydropyridines
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Moriel, Patricia
    Amar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) : 4792 - 4795
  • [3] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins
    Barluenga, José
    Moriel, Patricia
    Valdes, Carlos
    Aznar, Fernando
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5587 - 5590
  • [4] Synthesis of Enol Ethers and Enamines by Pd-Catalyzed Tosylhydrazide-Promoted Cross-Coupling Reactions
    Barluenga, Jose
    Escribano, Maria
    Moriel, Patricia
    Aznar, Fernando
    Valdes, Carlos
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (48) : 13291 - 13294
  • [5] Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin
    Bellina, Fabio
    Cauteruccio, Silvia
    Monti, Susanna
    Rossi, Renzo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (22) : 5757 - 5762
  • [6] SYNTHESIS AND EVALUATION OF STILBENE AND DIHYDROSTILBENE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS THAT INHIBIT TUBULIN POLYMERIZATION
    CUSHMAN, M
    NAGARATHNAM, D
    GOPAL, D
    CHAKRABORTI, AK
    LIN, CM
    HAMEL, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (08) : 2579 - 2588
  • [7] Dark GG, 1997, CANCER RES, V57, P1829
  • [8] The biological activity and chemistry of the southern African Combretaceae
    Eloff, J. N.
    Katerere, D. R.
    McGaw, L. J.
    [J]. JOURNAL OF ETHNOPHARMACOLOGY, 2008, 119 (03) : 686 - 699
  • [9] The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis
    Fulton, JR
    Aggarwal, VK
    de Vicente, J
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) : 1479 - 1492
  • [10] One-pot hydrosilylation-protodesilylation of functionalized diarylalkynes:: a highly selective access to Z-stilbenes.: Application to the synthesis of combretastatin A-4
    Giraud, Anne
    Provot, Olivier
    Harnze, Abdallah
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. TETRAHEDRON LETTERS, 2008, 49 (07) : 1107 - 1110