SYNTHESIS OF ISOQUINOLINES FROM INDANONES - TOTAL SYNTHESIS OF ILLUDININE

被引:0
|
作者
SHANKER, PS [1 ]
RAO, GSRS [1 ]
机构
[1] INDIAN INST SCI,DEPT ORGAN CHEM,BANGALORE 560012,KARNATAKA,INDIA
来源
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY | 1993年 / 32卷 / 12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
Schmidt reaction of 5-methoxy or 7-methoxyindan-1-ones or their derivatives results exclusively in isocarbostyrils which are converted into 6-methoxy or 8-methoxyisoquinolines in good yields. This strategy has been extended to the total synthesis of illudinine methyl ester (1b) starting from methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate (4).
引用
收藏
页码:1209 / 1213
页数:5
相关论文
共 50 条
  • [1] Synthesis of Illudinine from Dimedone
    Morrison, Alec E.
    Hoang, Tung T.
    Birepinte, Melodie
    Dudley, Gregory B.
    ORGANIC LETTERS, 2017, 19 (04) : 858 - 861
  • [2] TOTAL SYNTHESIS OF ILLUDININE, ILLUDALIC ACID, AND ILLUDACETALIC ACID
    WOODWARD, RB
    HOYE, TR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) : 8007 - 8014
  • [3] Concise synthesis of illudinine from dimedone
    Morrison, Alec
    Dudley, Gregory
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [4] SYNTHESIS OF ISOQUINOLINES FROM INDENES
    MILLER, RB
    FRINCKE, JM
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (26): : 5312 - 5315
  • [5] SYNTHESIS OF ISOQUINOLINES FROM INDENES
    DIME, DS
    MCLEAN, S
    JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24): : 4999 - 5000
  • [6] Regioselective Synthesis of Indanones
    van Leeuwen, Thomas
    Neubauer, Thomas M.
    Feringa, Ben L.
    SYNLETT, 2014, 25 (12) : 1717 - 1720
  • [7] Enantioselective Synthesis of Substituted Indanones from Silyloxyallenes
    Brekan, Jonathan A.
    Reynolds, Troy E.
    Scheidt, Karl A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1472 - +
  • [8] Synthesis of Illudinine from Dimedone and Identification of Activity as a Monoamine Oxidase Inhibitor
    Gaston, Robert, Jr.
    Geldenhuys, Werner J.
    Dudley, Gregory B.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21): : 13429 - 13437
  • [9] REARRANGEMENT IN SYNTHESIS OF ISOQUINOLINES FROM BENZYLAMINOACETONITRILES
    HARCOURT, DN
    TAYLOR, N
    WAIGH, RD
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (11) : 643 - &
  • [10] Microwave-mediated Nickel-catalyzed cyclotrimerization reactions: Total synthesis of illudinine
    Teske, Jesse A.
    Deiters, Alexander
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01): : 342 - 345