Combinatorial synthesis of heterocycles: Solid phase synthesis of 2-arylquinoline-4-carboxylic acid derivatives

被引:44
作者
Gopalsamy, A
Pallai, PV
机构
[1] Department of Rational Drug Design, Procept, Inc., Cambridge, MA 02139
[2] FMC Corporation, Discovery Research, Box 8, Princeton
关键词
D O I
10.1016/S0040-4039(96)02456-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Doebner quinoline synthesis has been adopted to solid phase. Acylation of an amino acid coupled to the Rink polystyrene resin with pyruvyl chloride afforded the immobilized amide 11. Further reaction of 11 with the preformed Schiffs base 12 or aldehyde 3 and aniline 2 gave, after trifluoroacetic acid cleavage, 2-arylquinoline-4-carboxylic acid amides 14 in good yields. (C) 1997, Elsevier Science Ltd.
引用
收藏
页码:907 / 910
页数:4
相关论文
共 25 条
  • [1] CZARNIK AW, 1996, ACCOUNTS CHEM RES, V29, P111
  • [2] DABHI TP, 1993, J INDIAN CHEM SOC, V70, P597
  • [3] Synthesis of ketones and aldehydes via reactions of Weinreb-type amides on solid support
    Dinh, TQ
    Armstrong, RW
    [J]. TETRAHEDRON LETTERS, 1996, 37 (08) : 1161 - 1164
  • [4] DOEBNER O, 1883, BER, V16, P2357
  • [5] FARINA C, 1995, Patent No. 32948
  • [6] GENERAL-METHOD FOR RAPID SYNTHESIS OF MULTICOMPONENT PEPTIDE MIXTURES
    FURKA, A
    SEBESTYEN, F
    ASGEDOM, M
    DIBO, G
    [J]. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 37 (06): : 487 - 493
  • [7] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .1. BACKGROUND AND PEPTIDE COMBINATORIAL LIBRARIES
    GALLOP, MA
    BARRETT, RW
    DOWER, WJ
    FODOR, SPA
    GORDON, EM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) : 1233 - 1251
  • [8] 2-Phenyl-4-quinolinecarboxamides: A novel class of potent and selective non-peptide competitive antagonists for the human neurokinin-3 receptor
    Giardina, GAM
    Sarau, HM
    Farina, C
    Medhurst, AD
    Grugni, M
    Foley, JJ
    Raveglia, LF
    Schmidt, DB
    Rigolio, R
    Vassallo, M
    Vecchietti, V
    Hay, DWP
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (12) : 2281 - 2284
  • [9] Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines
    Gordeev, MF
    Patel, DV
    Gordon, EM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) : 924 - 928
  • [10] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS
    GORDON, EM
    BARRETT, RW
    DOWER, WJ
    FODOR, SPA
    GALLOP, MA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) : 1385 - 1401