Aromatic ring hydroxylation of flavanones by dimethyldioxirane

被引：11
|
作者：
Bernini, R
Mincione, E
Sanetti, A
Mezzetti, M
Bovicelli, P
机构：
[1] Univ Tuscia, Diipartimento ABAC, I-01100 Viterbo, Italy
[2] Univ La Sapienza, CNR, Ctr Studio Chim Sostanze Organ Nat, I-00185 Rome 62, Italy
[3] Univ La Sapienza, Dipartimento Chim, I-00185 Rome 62, Italy
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 07期
关键词：
dioxirane; flavanones; hydroxylation;
D O I：
10.1016/S0040-4039(99)02236-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The selective and efficient oxidation of flavanones with dimethyldioxirane (DMD) is reported. Aromatic rings carrying methoxy groups were selectively hydroxylated in neutral and acidic media. In the latter case inversion of chemoselectivity with respect to the benzylethereal position was observed. This behaviour was exploited to obtain polyhydroxylated flavanones, which are compounds with potential antioxidant and biological properties. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1087 / 1090
页数：4
相关论文
共 50 条
  • [21] Enzymatic hydroxylation of aromatic compounds
    Ullrich, Rene
    Hofrichter, Martin
    CELLULAR AND MOLECULAR LIFE SCIENCES, 2007, 64 (03) : 271 - 293
  • [22] Nucleophilic Functionalizations of Aniline Derivatives: Aromatic Pummerer Reaction for Umpolung Halogenation and Hydroxylation on Benzene Ring
    Bao, Xingping
    Yao, Jinzhong
    Zhou, Hongwei
    Xu, Guangyu
    ORGANIC LETTERS, 2017, 19 (21) : 5780 - 5782
  • [23] AROMATIC HYDROXYLATION AS AN ANALYTICAL REACTION
    CONNORS, KA
    ALBERT, KS
    ANALYTICAL CHEMISTRY, 1972, 44 (04) : 879 - &
  • [24] THE DIRECT HYDROXYLATION OF AROMATIC COMPOUNDS
    BRADLEY, W
    CHEMISTRY & INDUSTRY, 1954, (22) : 631 - 633
  • [25] Enzymatic hydroxylation of aromatic compounds
    René Ullrich
    Martin Hofrichter
    Cellular and Molecular Life Sciences, 2007, 64 : 271 - 293
  • [26] HYDROXYLATION OF AROMATIC HYDROCARBONS IN RAT
    BAKKE, OM
    SCHELINE, RR
    TOXICOLOGY AND APPLIED PHARMACOLOGY, 1970, 16 (03) : 691 - &
  • [27] ENZYMATIC HYDROXYLATION OF AROMATIC COMPOUNDS
    MITOMA, C
    POSNER, HS
    REITZ, HC
    UDENFRIEND, S
    ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1956, 61 (02) : 431 - 441
  • [28] ANODIC HYDROXYLATION OF AROMATIC COMPOUNDS
    PAPOUCHADO, L
    PETRIE, G
    SHARP, JH
    ADAMS, RN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) : 5620 - +
  • [29] ENZYMATIC HYDROXYLATION OF AROMATIC DRUGS
    MITOMA, C
    UDENFRIEND, S
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 1955, 113 (01): : 40 - 40
  • [30] HYDROXYLATION OF AROMATIC-COMPOUNDS
    SO, YH
    MILLER, LL
    SYNTHESIS-STUTTGART, 1976, (07): : 468 - 469
12345