Methyl 2-methoxytetrafluoropropionate as a synthetic equivalent of methyl trifluoropyruvate in the Claisen condensation. The first synthesis of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones

被引:31
|
作者
Irgashev, Roman A. [1 ]
Sosnovskikh, Vyacheslav Ya [1 ]
Kalinovich, Nataliya [2 ]
Kazakova, Olesya [2 ]
Roeschenthaler, Gerd-Volker [2 ]
机构
[1] Ural State Univ, Dept Chem, Ekaterinburg 620083, Russia
[2] Univ Bremen, Inst Inorgan & Phys Chem, D-28334 Bremen, Germany
关键词
Methyl; 2-methoxytetrafluoropropionate; Acetophenones; Claisen condensation; Deprotection; Trifluoromethyl 1,2,4-triketones; NICOTINIC-ACID DERIVATIVES; 3,3,3-TRIFLUOROPYRUVATE; 3-(POLYFLUOROACYL)CHROMONES; BENZOPYRONES; TAUTOMERISM; CHEMISTRY; PRODUCTS; ENAMINES;
D O I
10.1016/j.tetlet.2009.06.067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-(Trifluoroacetyl)chromones and 5-aryl-2-liydroxy-2-(trifluoromethyl)furan-3(2H)-ones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4903 / 4905
页数:3
相关论文
共 50 条
  • [1] Synthesis of 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones and their reactions with aromatic 1,2-diamines, hydrazine and hydroxylamine
    Safrygin, Alexander V.
    Irgashev, Roman A.
    Slepukhin, Pavel A.
    Roeschenthaler, Gerd-Volker
    Sosnovskikh, Vyacheslav Y.
    TETRAHEDRON, 2015, 71 (45) : 8535 - 8543
  • [2] Chemistry of 2-ylidenefuran-3(2H)-ones: XIX. Reaction of 5-aryl-2(oxoylidene)furan-3(2H)-ones with carboxylic acid hydrazides
    E. N. Koz’minykh
    V. I. Goncharov
    V. O. Koz’minykh
    Russian Journal of Organic Chemistry, 2007, 43 : 864 - 867
  • [3] Chemistry of 2-ylidenefuran-3(2H)-ones:: XIX.: Reaction of 5-aryl-2(oxoylidene)furan-3(2H)-ones with carboxylic acid hydrazides
    Koz'minykh, E. N.
    Goncharov, V. I.
    Koz'minykh, V. O.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (06) : 864 - 867
  • [4] A simple and general synthesis of 2,2,4,5-tetrasubstituted furan-3(2H)-ones
    Kawaguchi, T
    Yasuta, S
    Inoue, Y
    SYNTHESIS-STUTTGART, 1996, (12): : 1431 - &
  • [5] SYNTHESIS AND BEHAVIOR OF 4-ETHOXYCARBONYL (2H) FURAN-3 ONES
    GELIN, R
    GALLIAUD, A
    CHANTEGREL, B
    GELIN, S
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE I-PHYSICOCHIMIE DES SYSTEMES LIQUIDES ELECTROCHIMIE CATALYSE GENIE CHIMIQUE, 1974, (5-6): : 1043 - 1047
  • [6] Chemistry of iminofurans: XII.1 Synthesis of 2-(arylimino)furan-3(2H)-ones and their reaction with amines
    E. R. Nasibullina
    A. N. Vasyanin
    S. N. Shurov
    A. E. Rubtsov
    Russian Journal of Organic Chemistry, 2016, 52 : 848 - 856
  • [7] Chemistry of iminofurans: XII.1 Synthesis of 2-(arylimino)furan-3(2H)-ones and their reaction with amines
    Nasibullina, E. R.
    Vasyanin, A. N.
    Shurov, S. N.
    Rubtsov, A. E.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (06) : 848 - 856
  • [8] A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one
    Bazhin, Denis N.
    Kudyakova, Yulia S.
    Roeschenthaler, Gerd-Volker
    Burgart, Yanina V.
    Slepukhin, Pavel A.
    Isenov, Maksim L.
    Saloutin, Victor I.
    Charushin, Valery N.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5236 - 5245
  • [9] SYNTHETIC STUDIES DIRECTED TOWARD THE PSEUROTINS .2. SYNTHESIS OF RELATED HIGHLY FUNCTIONALIZED FURAN-3(2H)-ONES
    SHAO, X
    DOLDER, M
    TAMM, C
    HELVETICA CHIMICA ACTA, 1990, 73 (02) : 483 - 491
  • [10] SYNTHESIS AND PHARMACOLOGICAL STUDY OF 5-ARYL-6-METHYL-4,5-DIHYDRO-PYRIDAZIN-3(2H)ONES AND RELATED 5-ARYL-6-METHYL-PYRIDAZIN-3(2H)ONES
    PINNA, GA
    CURZU, MM
    BARLOCCO, D
    CIGNARELLA, G
    CAVALLETTI, E
    GERMINI, M
    BERGER, K
    FARMACO-EDIZIONE SCIENTIFICA, 1988, 43 (06): : 539 - 549