Reaction of thioglycolate with alpha-fluoro-beta-(phenylthio)enones (or -enals): Synthesis of substituted alpha-carboxy-gamma-fluorothiophenes

被引：11
作者：
Andres, DF [1 ]
Laurent, EG [1 ]
Marquet, BS [1 ]
机构：
[1] UNIV LYON 1, LAB CHIM ORGAN 3, CNRS, F-69622 VILLEURBANNE, FRANCE
来源：
TETRAHEDRON LETTERS | 1997年 / 38卷 / 06期
关键词：
D O I：
10.1016/S0040-4039(96)02509-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthetic method to substituted alpha-carboxy-gamma-fluorothiophenes 2F is reported. They were prepared by the reaction between two equivalents of methyl thioglycolate anion and alpha-fluoro-beta-(phenylthio)enones (or -enals) 1F, in DMSO (70 degrees C) in yields ranging from 41% to 85%. We show from the reaction of (Z)-alpha-fluoro-beta-(phenylthio)but-enone 1aF, that cyclisation to fluorothiophene 2aF occurs via the formation of stable enolates of alpha-fluoro-beta-(dithianyl)butanone. (C) 1997, Elsevier Science Ltd.
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页码：1049 / 1052
页数：4
相关论文
共 14 条
  • [1] REGIOSELECTIVE SYNTHESIS OF 2-FUNCTIONALIZED THIOPHENES BY CONDENSATION OF ALPHA-MERCAPTO COMPOUNDS WITH BETA-AMINOENONE DERIVATIVES
    ALBEROLA, A
    ANDRES, JM
    GONZALEZ, A
    PEDROSA, R
    PRADANOS, P
    [J]. SYNTHETIC COMMUNICATIONS, 1990, 20 (16) : 2537 - 2547
  • [2] ANDRES D, IN PRESS TETRAHEDRON
  • [3] KINETICS OF THE REACTION OF BETA-METHOXY-ALPHA-NITROSTILBENE WITH THIOLATE IONS - 1ST DIRECT OBSERVATION OF THE INTERMEDIATE IN A NUCLEOPHILIC VINYLIC SUBSTITUTION
    BERNASCONI, CF
    KILLION, RB
    FASSBERG, J
    RAPPOPORT, Z
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) : 6862 - 6864
  • [4] FLUORO HETEROCYCLES WITH 5-MEMBERED RINGS
    BURGER, K
    WUCHERPFENNIG, U
    BRUNNER, E
    [J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 60, 1994, 60 : 1 - 64
  • [5] CERICHELLI G, 1990, GAZZ CHIM ITAL, V120, P749
  • [6] A CONVENIENT SYNTHESIS OF 3-FLUOROTHIOPHENE
    ELKASSMI, A
    FACHE, F
    LEMAIRE, M
    [J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (01) : 95 - 101
  • [7] POLY(3-FLUOROTHIOPHENE)
    ELKASSMI, A
    FACHE, F
    LEMAIRE, M
    [J]. JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1994, 373 (1-2): : 241 - 244
  • [8] PERLMUTTER P, 1992, TETRAHEDRON ORGANIC, V9, P13
  • [9] REINECKE MG, 1986, HETEROCYCL COMPOUNDS, V44, P79
  • [10] CONJUGATED POLY(THIOPHENES) - SYNTHESIS, FUNCTIONALIZATION, AND APPLICATIONS
    RONCALI, J
    [J]. CHEMICAL REVIEWS, 1992, 92 (04) : 711 - 738
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