First halogen-dance reaction in quinoline series:: application to a new synthesis of quindoline.

被引:46
作者
Arzel, E [1 ]
Rocca, P [1 ]
Marsais, F [1 ]
Godard, A [1 ]
Quéguiner, G [1 ]
机构
[1] INSA Rouen, IRCOF, UPRESA 6014 CNRS, F-76131 Mt St Aignan, France
关键词
halogen and compounds; metalation; polycyclic heterocyclic compounds; coupling reactions;
D O I
10.1016/S0040-4039(98)01386-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first halogen-dance reaction in quinoline series is described as well as a new convergent synthesis of quindoline, a natural benzo-delta-carboline. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6465 / 6466
页数:2
相关论文
共 9 条
  • [1] Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities
    Bierer, DE
    Fort, DM
    Mendez, CD
    Luo, J
    Imbach, PA
    Dubenko, LG
    Jolad, SD
    Gerber, RE
    Litvak, J
    Lu, Q
    Zhang, PS
    Reed, MJ
    Waldeck, N
    Bruening, RC
    Noamesi, BK
    Hector, RF
    Carlson, TJ
    King, SR
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) : 894 - 901
  • [2] CONSTITUENTS OF WEST-AFRICAN MEDICINAL-PLANTS .20. QUINDOLINE FROM CRYPTOLEPIS-SANGUINOLENTA
    DWUMABADU, D
    AYIM, JSK
    FIAGBE, NIY
    KNAPP, JE
    SCHIFF, PL
    SLATKIN, DJ
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1978, 67 (03) : 433 - 434
  • [3] Metallation in connection with cross-coupling reactions. Coupling of hindered aryls for the synthesis of 4-phenylpyridines as part of Streptonigrin and Lavendamycin analogues
    Godard, A
    Rocca, P
    Pomel, V
    ThomasditDumont, L
    Rovera, JC
    Thaburet, JF
    Marsais, F
    Queguiner, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 517 (1-2) : 25 - 36
  • [4] THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYLBORONIC ACID WITH HALOARENES IN THE PRESENCE OF BASES
    MIYAURA, N
    YANAGI, T
    SUZUKI, A
    [J]. SYNTHETIC COMMUNICATIONS, 1981, 11 (07) : 513 - 519
  • [5] DIRECTED METALATION OF PI-DEFICIENT AZAAROMATICS - STRATEGIES OF FUNCTIONALIZATION OF PYRIDINES, QUINOLINES, AND DIAZINES
    QUEGUINER, G
    MARSAIS, F
    SNIECKUS, V
    EPSZTAJN, J
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1991, 52 : 187 - 304
  • [6] CONNECTION BETWEEN METALATION AND CROSS-COUPLING STRATEGIES - A NEW CONVERGENT ROUTE TO AZACARBAZOLES
    ROCCA, P
    MARSAIS, F
    GODARD, A
    QUEGUINER, G
    [J]. TETRAHEDRON, 1993, 49 (01) : 49 - 64
  • [7] 1ST METALATION OF ARYL IODIDES - DIRECTED ORTHO-LITHIATION OF IODOPYRIDINES, HALOGEN-DANCE, AND APPLICATION TO SYNTHESIS
    ROCCA, P
    COCHENNEC, C
    MARSAIS, F
    THOMASDITDUMONT, L
    MALLET, M
    GODARD, A
    QUEGUINER, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) : 7832 - 7838
  • [8] THE PREPARATION OF HETEROCYCLIC FLUORINE COMPOUNDS BY THE SCHIEMANN REACTION .2. THE MONOFLUOROQUINOLINES
    ROE, A
    HAWKINS, GF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (05) : 1785 - 1786
  • [9] TOTAL ASSIGNMENT OF THE PROTON AND CARBON NMR-SPECTRA OF THE ALKALOID QUINDOLINE - UTILIZATION OF HMQC-TOCSY TO INDIRECTLY ESTABLISH PROTONATED CARBON-PROTONATED CARBON CONNECTIVITIES
    SPITZER, TD
    CROUCH, RC
    MARTIN, GE
    SHARAF, MHM
    SCHIFF, PL
    TACKIE, AN
    BOYE, GL
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (08) : 2065 - 2070