The first synthesis of 4-unsubstituted 3-(trifluoroacetyl)coumarins by the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by chromene-coumarin recyclization

被引：33
作者：
Chizhov, Dmitrii L. [1 ]
Sosnovskikh, Vyacheslav Ya. [2 ]
Pryadeina, Marina V. [1 ]
Burgart, Yanina V. [1 ]
Saloutin, Victor I. [1 ]
Charushin, Valery N. [1 ]
机构：
[1] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ural Branch, Ekaterinburg 620041, Russia
[2] Ural State Univ, Dept Chem, Ekaterinburg 620083, Russia
来源：
SYNLETT | 2008年 / 02期
关键词：
ethyl trifluoroacetoacetate; salicylaldehydes; Knoevenagel condensation; 3-(trifluoroacetyl)coumarins; chromene-coumarin recyclization;
D O I：
10.1055/s-2007-1000867
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of ethyl 6-substituted 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates was obtained in good yields via the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate in the presence of piperidinium acetate. The subsequent recyclization of these chromenes proceeds smoothly in refluxing chlorobenzene in the presence of p-toluenesulfonic acid affording previously unknown 3-(trifluoroacetyl)coumarins in moderate to good yields.
引用
收藏
页码：281 / 285
页数：5
相关论文
共 43 条
  • [1] AGUEZUBIS JCR, 2000, LUMINESCENCE, V15, P331
  • [2] BEIFUSS LF, 1991, COMPREHENSIVE ORGANI, V2, P341
  • [3] Synthesis of Nε-(7-diethylaminocoumarin-3-carboxyl)- and Nε-(7-methoxycoumarin-3-carboxyl)-L-Fmoc lysine as tools for protease cleavage detection by fluorescence
    Berthelot, T
    Talbot, JC
    Laïn, G
    Déleris, G
    Latxague, L
    [J]. JOURNAL OF PEPTIDE SCIENCE, 2005, 11 (03) : 153 - 160
  • [4] Montmorillonite KSF as an inorganic, water stable, and reusable catalyst for the knoevenagel synthesis of coumarin-3-carboxylic acids
    Bigi, F
    Chesini, L
    Maggi, R
    Sartori, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 1033 - 1035
  • [5] Coumarins: Fast synthesis by Knoevenagel condensation under microwave irradiation
    Bogdal, D
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 1998, (08): : 468 - 469
  • [6] Synthesis via carbon suboxide and pharmacological activity of coumarin derivatives
    Bonsignore, L
    Cottiglia, F
    Lavagna, SM
    Loy, G
    Secci, D
    [J]. FARMACO, 1998, 53 (10-11): : 693 - 697
  • [7] OXYGEN HETEROCYCLES .8. AROYLBENZOFURANS, AROYLDIBENZOFURANS, AND AROYLCOUMARINS OF POTENTIAL BIOLOGICAL INTEREST
    BUUHOI, NP
    SAINTRUF, G
    LOC, TB
    XUONG, ND
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JUN): : 2593 - 2596
  • [8] Reactions of fluoroalkyl-containing bis-β-diketones with hydrazine and hydroxylamine
    Chizhov, DL
    Ratner, VG
    Pashkevich, KI
    [J]. RUSSIAN CHEMICAL BULLETIN, 1999, 48 (04) : 758 - 760
  • [9] 2,4-bridged 1,5-bis(fluoroalkyl)-1,3,5-triketones:: synthesis and properties
    Chizhov, DL
    Pashkevich, KI
    Röschenthaler, GV
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 123 (02) : 267 - 272
  • [10] Recent advances in the chemistry of α,β-unsaturated trifluoromethylketones
    Druzhinin, Sergey V.
    Balenkova, Elizabeth S.
    Nenajdenko, Valentine G.
    [J]. TETRAHEDRON, 2007, 63 (33) : 7753 - 7808
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