Synthesis of pyranoquinoline alkaloids via (4+2) cycloaddition reaction

被引:0
|
作者
Suresh, T [1 ]
Dhanabal, T [1 ]
Kumar, RN [1 ]
Mohan, PS [1 ]
机构
[1] Bharathiar Univ, Dept Chem, Coimbatore 641046, Tamil Nadu, India
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
An easy route to synthesize pyranoquinoline based alkaloids like flindersine, haplamine, N-methylflindersine and its derivatives were performed from the respective 4-hydroxyquinolin-2(1H)-one, dimethyl acrylic acid and para formaldehyde through generation of O-quinone methide intermediates and subjecting (4+2) cycloaddition. Further, dihydro intermediates were oxidized by DDQ.
引用
收藏
页码:79 / 84
页数:6
相关论文
共 50 条
  • [11] Improved Total Synthesis of Indolizidine and Quinolizidine Alkaloids via Nickel-Catalyzed (4+2) Cycloaddition
    Renner, Jonas
    Smith, Sleight R.
    Cowley, Jacob M.
    Louie, Janis
    JOURNAL OF ORGANIC CHEMISTRY, 2022, : 8871 - 8883
  • [12] [4+2]CYCLOADDITION REACTION OF HETERODIENE
    OHNO, M
    SASAKI, T
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1984, 42 (02) : 125 - 142
  • [13] Synthesis of Diazanorcaradienes and 1,2-Diazepines via the Tandem [4+2]-Cycloaddition/Retro-[4+2]-Cycloaddition Reaction between Methoxycarbonylcyclopropenes and Dimethoxycarbonyltetrazine
    Belyy, Alexander Yu.
    Levina, Anastasia A.
    Platonov, Dmitry N.
    Salikov, Rinat F.
    Medvedev, Michael G.
    Tomilov, Yury V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (26) : 4133 - 4138
  • [14] Enantioselective [4+2] Cycloaddition/Cyclization Cascade Reaction and Total Synthesis of cis-Bis(cyclotryptamine) Alkaloids
    Xu, Jian
    Li, Runze
    Xu, Nian
    Liu, Xiaohua
    Wang, Fei
    Feng, Xiaoming
    ORGANIC LETTERS, 2021, 23 (05) : 1856 - 1861
  • [15] Synthesis of 2,3-dihydro-4-pyranones from epoxides via intermolecular [4+2] cycloaddition reaction
    Indukuri, Kiran
    Bondalapati, Somasekhar
    Sultana, Sabera
    Saikia, Anil Kumar
    RSC ADVANCES, 2012, 2 (25): : 9398 - 9402
  • [16] SYNTHESIS OF SOME NEW POLYNUCLEAR COMPOUNDS BY [4+2] CYCLOADDITION REACTION
    SAMANTA, SR
    MUKHERJEE, AK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1987, 26 (01): : 26 - 29
  • [17] SYNTHESIS OF SOME NEW POLYNUCLEAR COMPOUNDS BY [4+2]-CYCLOADDITION REACTION
    SAMANTA, SR
    MUKHERJEE, AK
    BHATTACHARYYA, AJ
    CURRENT SCIENCE, 1988, 57 (17): : 926 - 931
  • [18] On the [4+2]-cycloaddition reaction of levoglucosenone with piperylene
    Valeev, FA
    Gaisina, IN
    Miftakhov, MS
    RUSSIAN CHEMICAL BULLETIN, 1996, 45 (10) : 2453 - 2455
  • [19] Stereoselective synthesis of tetrahydropyrans via a formal [4+2]-cycloaddition of allylsilanes
    Angle, SR
    El-Said, NA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (43) : 10211 - 10212
  • [20] Total synthesis of (±)-strychnine via a [4+2]-cycloaddition/rearrangement cascade
    Zhang, Hongjun
    Boonsombat, Jutatip
    Padwa, Albert
    ORGANIC LETTERS, 2007, 9 (02) : 279 - 282