EPOXIDATION OF FLAVONES BY DIMETHYLDIOXIRANE

被引:51
|
作者
ADAM, W [1 ]
GOLSCH, D [1 ]
HADJIARAPOGLOU, L [1 ]
PATONAY, T [1 ]
机构
[1] LAJOS KOSSUTH UNIV,DEPT ORGAN CHEM,H-4010 DEBRECEN,HUNGARY
来源
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 26期
关键词
D O I
10.1021/jo00026a020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, H-1 and C-13 NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.
引用
收藏
页码:7292 / 7297
页数:6
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 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
  • [3] DIMETHYLDIOXIRANE EPOXIDATION OF ENOL PHOSPHATES
    ADAM, W
    HADJIARAPOGLOU, L
    KLICIC, J
    TETRAHEDRON LETTERS, 1990, 31 (45) : 6517 - 6520
  • [4] Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane
    Compton, Benjamin J.
    Larsen, Lesley
    Weavers, Rex T.
    TETRAHEDRON, 2011, 67 (04) : 718 - 726
  • [5] DIMETHYLDIOXIRANE EPOXIDATION OF AURONES AND ISOFLAVONES
    ADAM, W
    HADJIARAPOGLOU, L
    LEVAI, A
    SYNTHESIS-STUTTGART, 1992, (05): : 436 - 438
  • [6] 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
  • [7] 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
  • [8] Epoxidation of limonene and pinenes by dimethyldioxirane in microemulsions
    Ahmat, Yacoub Mahamat
    Kaliaguine, Serge
    CATALYSIS TODAY, 2023, 407 : 146 - 155
  • [9] Dimethyldioxirane epoxidation of polycyclic fluoranthene hydrocarbons
    Liu, FS
    Cho, BP
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (15) : 2181 - 2184
  • [10] Selective epoxidation of polar substrates by dimethyldioxirane
    Puyau, PD
    Perie, JJ
    SYNTHETIC COMMUNICATIONS, 1998, 28 (14) : 2679 - 2683