An efficient synthesis of 3-cyanoquinoline derivatives

被引:37
作者
Charpentier, P [1 ]
Lobrégat, V [1 ]
Levacher, V [1 ]
Dupas, G [1 ]
Quéguiner, G [1 ]
Bourguignon, J [1 ]
机构
[1] IRCOF, INSA, CNRS, Lab Chim Organ Fine & Heterocycl, F-76131 Mt St Aignan, France
关键词
D O I
10.1016/S0040-4039(98)00677-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short aid efficient method is reported for the preparation of 3-cyanoquinoline derivatives. Reaction of 3,3-dimethoxy-2-formyl-propanenitrile sodium salt 1 with various anilines 2 afforded (E) enamines 3 which were subsequently isomerized into (Z) enamines 4 and cyclized in a one pot procedure to give 3-cyanoquinolines 5 in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4013 / 4016
页数:4
相关论文
共 15 条
  • [1] BENOIT R, 1987, SYNTHESIS-STUTTGART, P1124
  • [2] BERKOUS R, 1994, B SOC CHIM FR, V131, P632
  • [3] THE SKRAUP REACTION WITH M-SUBSTITUTED ANILINES
    BRADFORD, L
    ELLIOTT, TJ
    ROWE, FM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1947, (APR): : 437 - 445
  • [4] BICYCLIC COMPOUNDS AS RING-CONSTRAINED INHIBITORS OF PROTEIN-TYROSINE KINASE-P56LCK
    BURKE, TR
    LIM, B
    MARQUEZ, VE
    LI, ZH
    BOLEN, JB
    STEFANOVA, I
    HORAK, ID
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (04) : 425 - 432
  • [5] Eliel E. L., 1994, STEREOCHEMISTRY ORGA, P544
  • [6] ORTHO FUNCTIONALIZATION OF AROMATIC-AMINES - ORTHO LITHIATION OF N-PIVALOYLANILINES
    FUHRER, W
    GSCHWEND, HW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (07) : 1133 - 1136
  • [7] GURNOS J, 1977, CHEM HETEROCYCLIC CO, V32, P93
  • [8] HARRIS ND, 1973, SYNTHESIS-STUTTGART, P48
  • [9] Jansen HE, 1937, RECL TRAV CHIM PAY-B, V56, P709
  • [10] 2-(Trifluoromethyl)quinolines from anilines: A novel mode of isomerization and cyclization
    Keller, H
    Schlosser, M
    [J]. TETRAHEDRON, 1996, 52 (13) : 4637 - 4644