Chemistry of naphthazarin derivatives. Transetherification selectivity of naphthazarin methoxy derivatives

被引：5
|
作者：
Pokhilo, N. D. [1 ]
Denisenko, V. A. [1 ]
Anufriev, V. F. [1 ]
机构：
[1] Russian Acad Sci, Far Eastern Branch, Elyakov Pacific Inst Bioorgan Chem, Vladivostok 690022, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 50卷 / 05期
关键词：
ECHINOCHROME;
D O I：
10.1134/S1070428014050054
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Transetherification of naphthazarin methoxy derivatives in basic conditions occurs only with primary monohydric alcohols. 1,3-Butanediol due to the assistance of the hydroxy group at the C-1 atom gives rise to a mixture of transetherification products at the primary and secondary hydroxy groups in a ratio 3: 1. The reaction with methyl alpha-D-glucopyranoside affords predominantly methyl 6-O-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-alpha-D-glucopyranoside, previously unknown water-soluble naphthoquinone-carbohydrate conjugate.
引用
收藏
页码：647 / 653
页数：7
相关论文
共 50 条
  • [1] Chemistry of naphthazarin derivatives. Transetherification selectivity of naphthazarin methoxy derivatives
    N. D. Pokhilo
    V. A. Denisenko
    V. F. Anufriev
    Russian Journal of Organic Chemistry, 2014, 50 : 647 - 653
  • [2] Chemistry of naphthazarin derivatives: XV. Bromination of naphthazarin and its derivatives
    N. D. Pokhilo
    A. Ya. Yakubovskaya
    V. P. Glazunov
    Russian Journal of Organic Chemistry, 2011, 47
  • [3] Chemistry of naphthazarin derivatives: XV. Bromination of naphthazarin and its derivatives
    Pokhilo, N. D.
    Yakubovskaya, A. Ya.
    Glazunov, V. P.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (04) : 504 - 509
  • [4] Chemistry of naphthazarin derivatives. 11. Trisubstituted hydroquinone derivatives in the preparative synthesis of naphthazarins
    V. Ph. Anufriev
    S. G. Polonik
    N. D. Pokhilo
    N. N. Balanyova
    Russian Chemical Bulletin, 2003, 52 : 2247 - 2250
  • [5] Chemistry of naphthazarin derivatives. 9. Direct observation of prototropic tautomerism of (poly)hydroxynaphthazarins by IR spectroscopy
    V. P. Glazunov
    A. Ya. Yakubovskaya
    N. D. Pokhilo
    N. V. Bochinskaya
    V. Ph. Anufriev
    Russian Chemical Bulletin, 2003, 52 : 198 - 207
  • [6] The chemistry of naphthazarin derivatives 4. A simple preparative synthesis of mompain
    Malinovskaya, GV
    Chizhova, AY
    Anufriev, VF
    RUSSIAN CHEMICAL BULLETIN, 1999, 48 (05) : 1010 - 1011
  • [7] The chemistry of naphthazarin derivatives4. A simple preparative synthesis of mompain
    G. V. Malinovskaya
    A. Ya. Chizhova
    V. F. Anufriev
    Russian Chemical Bulletin, 1999, 48 : 1010 - 1011
  • [8] Chemistry of naphthazarin derivatives - 11. Trisubstituted hydroquinone derivatives in the preparative synthesis of naphthazarins
    Anufriev, VP
    Polonik, SG
    Pokhilo, ND
    Balanyova, NN
    RUSSIAN CHEMICAL BULLETIN, 2003, 52 (10) : 2247 - 2250
  • [9] The chemistry of naphthazarin derivatives3. Synthesis of the dideoxy analog of islandoquinone
    A. Ya. Chizhova
    T. Yu. Kochergina
    V. F. Anufriev
    V. A. Denisenko
    V. P. Glazunov
    Russian Chemical Bulletin, 1999, 48 : 938 - 943
  • [10] Chemistry of naphthazarin derivatives. 10. First direct observation of prototropic tautomerism of 1"-hydroxyalkylnaphthazarins by IR spectroscopy
    V. P. Glazunov
    N. D. Pokhilo
    N. V. Bochinskaya
    A. Ya. Yakubovskaya
    V. Ph. Anufriev
    Russian Chemical Bulletin, 2003, 52 : 1629 - 1632
12345