PREPARATION AND REACTIONS OF 1-(TERT-BUTYLDIMETHYLSILYL)-3-LITHIOINDOLE, REGIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED INDOLES

被引:59
作者
AMAT, M [1 ]
HADIDA, S [1 ]
SATHYANARAYANA, S [1 ]
BOSCH, J [1 ]
机构
[1] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1021/jo00080a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-(tert-Butyldimethylsilyl)-3-lithioindole (2) is prepared by metalation of the corresponding 3-bromo derivative 1 and efficiently reacts with electrophiles to give 3-substituted indoles 3 and 4. © 1994, American Chemical Society. All rights reserved.
引用
收藏
页码:10 / 11
页数:2
相关论文
共 43 条
  • [1] AN EFFICIENT SYNTHESIS OF 2-(2-PYRIDYL)INDOLES BY PALLADIUM(0)-CATALYZED HETEROARYLATION
    AMAT, M
    HADIDA, S
    BOSCH, J
    [J]. TETRAHEDRON LETTERS, 1993, 34 (31) : 5005 - 5006
  • [2] CYCLOHEXADIENONE ANNULATIONS OF ARYL CARBENE COMPLEXES OF CHROMIUM - NEW STRATEGIES FOR THE SYNTHESIS OF INDOLE ALKALOIDS
    BAUTA, WE
    WULFF, WD
    PAVKOVIC, SF
    ZALUZEC, EJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) : 3249 - 3252
  • [3] TOTAL SYNTHESIS OF YUEHCHUKENE
    BERGMAN, J
    VENEMALM, L
    [J]. TETRAHEDRON LETTERS, 1988, 29 (24) : 2993 - 2994
  • [4] NOVEL SYNTHESIS OF INDOLE ALKALOID ELLIPTICINE
    BESSELIEVRE, R
    THAL, C
    HUSSON, HP
    POTIER, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (03) : 90 - 91
  • [5] THE SYNTHESIS OF 4-SUBSTITUTED INDOLES VIA ARENETRICARBONYLCHROMIUM(O) COMPLEXES
    BESWICK, PJ
    GREENWOOD, CS
    MOWLEM, TJ
    NECHVATAL, G
    WIDDOWSON, DA
    [J]. TETRAHEDRON, 1988, 44 (23) : 7325 - 7334
  • [6] BRAY BL, 1990, J ORG CHEM, V55, P6137
  • [7] BUTTERY CD, 1991, SYNLETT, P315
  • [8] N-METHYL LITHIATION OF N-METHYLINDOLES DIRECTED BY ALPHA-AMINO ALKOXIDES
    COMINS, DL
    KILLPACK, MO
    [J]. TETRAHEDRON LETTERS, 1989, 30 (33) : 4337 - 4340
  • [9] LITHIATION OF HETEROCYCLES DIRECTED BY ALPHA-AMINO ALKOXIDES
    COMINS, DL
    KILLPACK, MO
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (01) : 104 - 109
  • [10] CONWAY SC, 1990, HETEROCYCLES, V30, P627