DIMETHYLDIOXIRANE EPOXIDATION OF AURONES AND ISOFLAVONES

被引:0
|
作者
ADAM, W [1 ]
HADJIARAPOGLOU, L [1 ]
LEVAI, A [1 ]
机构
[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY
来源
SYNTHESIS-STUTTGART | 1992年 / 05期
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
The synthesis of the corresponding epoxides 2 and 4 by epoxidation of aurones (2-benzylidenebenzofuran-3(2H)-ones, 1) and isoflavones (3-aryl-4H-1-benzopyran-4-ones, 3) with dimethyldioxirane at subambient temperatures is reported. These acid- and base-sensitive epoxides, which have been previously difficult to prepare, were isolated in excellent yields and were completely characterized by spectral and microanalytical data. The now readily available aurone and/or isoflavone oxides may serve as convenient precursors to flavonoid-type natural products.
引用
收藏
页码:436 / 438
页数:3
相关论文
共 50 条
  • [1] DIMETHYLDIOXIRANE EPOXIDATION OF FLAVONES
    ADAM, W
    GOLSCH, D
    HADJIARAPOGLOU, L
    PATONAY, T
    TETRAHEDRON LETTERS, 1991, 32 (08) : 1041 - 1044
  • [2] EPOXIDATION OF FLAVONES BY DIMETHYLDIOXIRANE
    ADAM, W
    GOLSCH, D
    HADJIARAPOGLOU, L
    PATONAY, T
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26): : 7292 - 7297
  • [3] General synthesis of flavones, aurones, and isoflavones
    Wei, JQ
    Kraus, GA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U37 - U37
  • [4] EPOXIDATION OF α,β-UNSATURATED ESTERS BY DIMETHYLDIOXIRANE
    Baumstark, A. L.
    Vasquez, P. C.
    Aly, M.
    Sansone, J. P.
    HETEROCYCLIC COMMUNICATIONS, 2010, 16 (2-3) : 183 - 186
  • [5] DIMETHYLDIOXIRANE EPOXIDATION OF ENOL PHOSPHATES
    ADAM, W
    HADJIARAPOGLOU, L
    KLICIC, J
    TETRAHEDRON LETTERS, 1990, 31 (45) : 6517 - 6520
  • [6] Enantioselective epoxidation of isoflavones by Jacobsen's Mn(III)salen catalysts and dimethyldioxirane oxygen-atom source
    Adam, W
    Fell, RT
    Lévai, A
    Patonay, T
    Peters, K
    Simon, A
    Tóth, G
    TETRAHEDRON-ASYMMETRY, 1998, 9 (07) : 1121 - 1124
  • [8] Diastereoselectivity in the epoxidation of substituted cyclohexenes by dimethyldioxirane
    Murray, RW
    Singh, M
    Williams, BL
    Moncrieff, HM
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (05): : 1830 - 1841
  • [9] Continuous dimethyldioxirane generation for polymer epoxidation
    Ahlqvist, Grace P.
    Burke, Eileen G.
    Johnson, Jeremiah A.
    Jamison, Timothy F.
    POLYMER CHEMISTRY, 2021, 12 (04) : 489 - 493
  • [10] Epoxidation of limonene and pinenes by dimethyldioxirane in microemulsions
    Ahmat, Yacoub Mahamat
    Kaliaguine, Serge
    CATALYSIS TODAY, 2023, 407 : 146 - 155