Application of Daugulis Copper-Catalyzed Direct Arylation to the Synthesis of 5-Aryl Benzotriazepines

被引:74
作者
Yotphan, Sirilata
Bergman, Robert G. [1 ]
Ellman, Jonathan A.
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
H BOND ACTIVATION; ANTAGONISTS; POTENT; FUNCTIONALIZATION; ALKENYLATION; QUINOLINES; INHIBITORS; DISCOVERY; PYRIDINES;
D O I
10.1021/ol900103a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the direct arylation of benzotriazepines is reported, employing an aryl iodide as the coupling partner, copper iodide as the catalyst, and lithium tert-butoxide as the base. A variety of electron-rich, electron-poor, and sterically hindered aryl iodides are compatible with the reaction conditions. The arylation reaction can also be performed outside a glovebox in air without a significant decrease in yield. Furthermore, convenient microwave conditions for carrying out this transformation are reported.
引用
收藏
页码:1511 / 1514
页数:4
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共 25 条
  • [1] 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
  • [2] Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines
    Berman, Ashley M.
    Lewis, Jared C.
    Bergman, Robert G.
    Ellman, Jonathan A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 14926 - +
  • [3] Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes
    Besselievre, Francois
    Piguel, Sandrine
    Mahuteau-Betzer, Florence
    Grierson, David S.
    [J]. ORGANIC LETTERS, 2008, 10 (18) : 4029 - 4032
  • [4] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES
    BUNIN, BA
    ELLMAN, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) : 10997 - 10998
  • [5] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
    Campeau, LC
    Fagnou, K
    [J]. CHEMICAL COMMUNICATIONS, 2006, (12) : 1253 - 1264
  • [6] Reactions of 1,4-benzodiazepinic N-nitrosoamidines with tosylmethyl isocyanide:: A novel synthesis of midazolam
    del Pozo, C
    Macías, A
    Alonso, E
    González, J
    [J]. SYNTHESIS-STUTTGART, 2004, (16): : 2697 - 2703
  • [7] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
    Do, Hien-Ouang
    Khan, Rana M. Kashif
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) : 15185 - 15192
  • [8] Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) : 1128 - +
  • [9] Copper-catalyzed arylation of heterocycle C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12404 - +
  • [10] METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS
    EVANS, BE
    RITTLE, KE
    BOCK, MG
    DIPARDO, RM
    FREIDINGER, RM
    WHITTER, WL
    LUNDELL, GF
    VEBER, DF
    ANDERSON, PS
    CHANG, RSL
    LOTTI, VJ
    CERINO, DJ
    CHEN, TB
    KLING, PJ
    KUNKEL, KA
    SPRINGER, JP
    HIRSHFIELD, J
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) : 2235 - 2246