Enantioselective Dearomative Cyclization of Homotryptamines with Allenamides into Indolo[2,3-b]quinolines

被引:16
|
作者
Biswas, Soumen [1 ,2 ]
Kim, Hanbyul [1 ,2 ]
Cao, Kiet Le Anh [1 ,2 ]
Shin, Seunghoon [1 ,2 ]
机构
[1] Hanyang Univ, Dept Chem, Res Inst Nat Sci, 222 Wangsimni Ro, Seoul 04763, South Korea
[2] Hanyang Univ, Ctr New Direct Organ Synth CNOS, 222 Wangsimni Ro, Seoul 04763, South Korea
基金
新加坡国家研究基金会;
关键词
dearomative cyclization; homotryptamine; indolo[2; 3-b]quinolines; chiral Bronsted acid catalysis; CATALYTIC ASYMMETRIC DEAROMATIZATION; 4+2 CYCLOADDITION; INDOLES; PYRROLOINDOLINES; CONSTRUCTION; STRATEGY; FACILE;
D O I
10.1002/adsc.202000083
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We have developed a catalytic asymmetric dearomative cyclization of homotryptamine derivatives, furnishing enantioenriched indolo[2,3-b]quinoline scaffolds. The activation of allenamides in the presence of chiral phosphoric acids triggered the dearomative cyclization in up to 99% ee.
引用
收藏
页码:1841 / 1845
页数:5
相关论文
共 50 条
  • [1] I+/TBHP Catalysis For Tandem Oxidative Cyclization To Indolo[2,3-b]quinolines
    Uyanik, Muhammet
    Tanaka, Hiroki
    Ishihara, Kazuaki
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (01) : 164 - 169
  • [2] Synthesis of Indolo- and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene Derivatives
    Khaikate, Onnicha
    Inthalaeng, Natthamon
    Meesin, Jatuporn
    Kantarod, Kritchasorn
    Pohmakotr, Manat
    Reutrakul, Vichai
    Soorukram, Darunee
    Leowanawat, Pawaret
    Kuhakarn, Chutima
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15131 - 15144
  • [3] Synthesis of Indolo[2,3-b]quinolines via a Visible Light-Induced Intramolecular Oxidative Cyclization and Detosylation
    You, F. B.
    Wang, J. G.
    Osman, S.
    Xia, X. D.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (06) : 1048 - 1058
  • [4] Synthesis of Indolo[2,3-b]quinolines via a Visible Light-Induced Intramolecular Oxidative Cyclization and Detosylation
    F. B. You
    J. G. Wang
    S. Osman
    X. D. Xia
    Russian Journal of Organic Chemistry, 2023, 59 : 1048 - 1058
  • [5] SOME TRANSFORMATIONS OF 2,3-DIAMINOINDOLE DERIVATIVES - SYNTHESIS OF INDOLO[2,3-B]QUINOLINES
    KURILO, GN
    ROSTOVA, NJ
    CHERKASOVA, AA
    GRINEV, AN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1977, (12): : 1645 - 1647
  • [6] Chemistry of substituted quinolines:: Thieno[2,3-b] and thiopyrano[2,3-b]quinolines
    Kiran, Balaji M.
    Nandeshwarappa, Belalakatte P.
    Vaidya, Vijayavittala P.
    Mahadevan, Kittappa M.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2007, 182 (05) : 969 - 980
  • [7] New glycoside derivatives of 6H-indolo [2,3-b]quinolines
    Badowska-Roslonek, K
    Kaczmarek, L
    Ramza, J
    Godlewska, J
    Opolski, A
    Peczynska-Czoch, W
    POLISH JOURNAL OF CHEMISTRY, 2005, 79 (02) : 369 - 386
  • [8] N-Bromosuccinimide as an efficient catalyst for the synthesis of indolo[2,3-b]quinolines
    Ghorbani-Vaghei, Ramin
    Malaekehpoor, Seyedeh Mina
    TETRAHEDRON LETTERS, 2012, 53 (35) : 4751 - 4753
  • [9] New Amino Acid Derivatives of 6H-Indolo[2,3-b]quinolines
    Sidoryk, K.
    Kaczmarek, L.
    Szczepek, W. J.
    Wietrzyk, J.
    Switalska, M.
    Peczynska-Czoch, W.
    POLISH JOURNAL OF CHEMISTRY, 2008, 82 (11) : 2095 - 2105
  • [10] Synthesis of Indolo[2,3-b]quinolines by Palladium-catalyzed Annulation of Unsaturated Isothioureas
    Takeda, Hiroshi
    Ishida, Takayuki
    Takemoto, Yoshiji
    CHEMISTRY LETTERS, 2009, 38 (08) : 772 - 773