A CONVENIENT SYNTHESIS OF 5-SUBSTITUTED-2,3-DIHYDROTHIOPHENES

被引:0
|
作者
ONEIL, IA [1 ]
HAMILTON, KM [1 ]
MILLER, JA [1 ]
YOUNG, RJ [1 ]
机构
[1] WELLCOME RES LABS,DEPT MED CHEM,BECKENHAM BR3 3BS,KENT,ENGLAND
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of gamma-thiobutyrolactone with KHMDS and N-(5-chloro-2-pyridyl)triflimide (Comin's reagent) gives the corresponding thiolenoltriflate in good yield. Coupling of the thiolenortriflate with Gilman cuprates proceeds smoothly to give the 5-substituted-2,3-dihydrothiophenes. The synthesis of a homochiral thiolactone is described. Conversion to the corresponding thiolenoltriflate proceeds in good yield using the conditions described above. The coupling with Gilman cuprates gives homochiral 5-substituted-2,3-dihydrothiophenes in good yield.
引用
收藏
页码:151 / 152
页数:2
相关论文
共 50 条
  • [11] LIGHT-INDUCED SYNTHESIS OF THIOLANES AND 2,3-DIHYDROTHIOPHENES BY ADDITION OF (E)-4-MERCAPTO-2-BUTENOATES TO ALKENES OR ALKYNES
    ANKLAM, E
    MARGARETHA, P
    HELVETICA CHIMICA ACTA, 1984, 67 (08) : 2198 - 2205
  • [12] SYNTHESIS AND HERBICIDAL ACTIVITY OF 5-SUBSTITUTED-2,4-IMIDAZOLIDINEDIONES
    WEE, SH
    PRISBYLLA, MP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 24 - AGRO
  • [13] Copper-catalyzed tandem S-alkylation and S-alkenylation of sodium sulfide: synthesis of 2,3-dihydrothiophenes and thiophenes
    Liao, Qian
    You, Wei
    Lou, Zhen-Bang
    Wen, Li-Rong
    Xi, Chanjuan
    TETRAHEDRON LETTERS, 2013, 54 (11) : 1475 - 1477
  • [14] CONVERSION OF 3-CYCLOPENTENYL HYDROPEROXIDE INTO 5-SUBSTITUTED-2,3-DIOXABICYCLO[2.2.1]HEPTANES
    BLOODWORTH, AJ
    EGGELTE, HJ
    TETRAHEDRON LETTERS, 1980, 21 (20) : 2001 - 2004
  • [15] Reactions of polyfluorinated thietanes Selective synthesis of 4-R-2,2-bis(trifluoromethyl)thietane-1-S-oxides and 2-substituted 5-fluoro-4-(trifluoromethyl)-2,3-dihydrothiophenes
    Petrov, Viacheslav A.
    Marshall, William J.
    JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (09) : 780 - 787
  • [16] Synthesis, biological activity, and mechanism of 5-substituted-2,4-diaminoquinazolines.
    Swayze, JK
    Canada, EJ
    Carroll, CJ
    Durst, GL
    Erickson, JA
    Galka, CS
    Green, FR
    Hannum, AC
    Henry, MJ
    Lawler, LK
    Rezac, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U53 - U53
  • [17] Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives
    Peyron, C
    Benhida, R
    Bories, C
    Loiseau, PM
    BIOORGANIC CHEMISTRY, 2005, 33 (06) : 439 - 447
  • [18] Microwave-accelerated diastereoselective catalyst-free one-pot four-component synthesis of 2-(N-carbamoylacetamide)-substituted 2,3-dihydrothiophenes in glycerol
    Reza Kordnezhadian
    Mohsen Shekouhy
    Ali Khalafi-Nezhad
    Molecular Diversity, 2020, 24 : 737 - 751
  • [19] A GENERAL PROCEDURE FOR THE SYNTHESIS OF NOVEL 5-SUBSTITUTED-2,4-DIMETHOXYPYRIMIDINES AND 5-SUBSTITUTED URACILS
    KUNDU, NG
    CHOUDHURI, LN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 280 - ORGN
  • [20] Microwave-accelerated diastereoselective catalyst-free one-pot four-component synthesis of 2-(N-carbamoylacetamide)-substituted 2,3-dihydrothiophenes in glycerol
    Kordnezhadian, Reza
    Shekouhy, Mohsen
    Khalafi-Nezhad, Ali
    MOLECULAR DIVERSITY, 2020, 24 (03) : 737 - 751