Versatile synthesis of 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones

被引:19
|
作者
Püschl, A
Rudbeck, HC
Faldt, A
Confante, A
Kehler, J
机构
[1] H Lundbeck & Co AS, Med Chem Res, DK-2500 Copenhagen, Denmark
[2] H Lundbeck & Co AS, Proc Res, DK-2500 Copenhagen, Denmark
来源
SYNTHESIS-STUTTGART | 2005年 / 02期
关键词
3-arylindan-1-ones; palladium; reductive cyclization; chalcone; intramolecular;
D O I
10.1055/s-2004-834929
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have developed a novel and versatile synthesis of racemic 3-arylindan-1-ones by palladium-catalyzed intramolecular reductive cyclization of bromochalcones. This method is especially attractive because it avoids strong acidic conditions and consequently a larger number of sensitive functional groups are accepted during synthesis compared with existing methods.
引用
收藏
页码:291 / 295
页数:5
相关论文
共 50 条
  • [21] Silver-Promoted Rapid Synthesis of 3-Arylindan-1-ones: Microwave-Assisted Reductive Coupling of N-Tosylhydrazone and Boronic Acids
    Tamizharasan, Natarajan
    Santhoshkumar, Pandeeswaran
    Devarajan, Nainamalai
    Hallur, Mahanandeesha S.
    Hallur, Gurulingappa
    Suresh, Palaniswamy
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7417 - 7428
  • [22] Palladium-Catalyzed Intramolecular Cyclization of Ynamides: Synthesis of 4-Halo-oxazolones
    Huang, Hai
    He, Guangke
    Zhu, Guohao
    Zhu, Xiaolin
    Qiu, Shineng
    Zhu, Hongjun
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07): : 3480 - 3487
  • [23] Palladium-catalyzed tandem cyclization and dimerization of (Z)-3-iodo-3-alken-1-ones
    Luo, FT
    Bajji, AC
    Jeevanandam, A
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05): : 1738 - 1740
  • [24] Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of β-Nitrostyrenes with Phenyl Formate as a CO Surrogate
    Ferretti, Francesco
    Fouad, Manar Ahmed
    Ragaini, Fabio
    CATALYSTS, 2022, 12 (01)
  • [25] Synthesis of imidazoisoindol-3-ones by a palladium-catalyzed intramolecular C-H insertion reaction
    Dandepally, Srinivasa Reddy
    Williams, Alfred L.
    TETRAHEDRON LETTERS, 2009, 50 (13) : 1395 - 1398
  • [26] A new palladium-catalyzed intramolecular cyclization: Synthesis of 1-aminoindole derivatives and functionalization of their carbocylic rings
    Watanabe, M
    Yamamoto, T
    Nishiyama, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (14) : 2501 - +
  • [27] Synthesis of Phenanthrenes through Visible-Light Photoredox Catalyzed Intramolecular Cyclization of -Bromochalcones
    Nagode, Savita B.
    Kant, Ruchir
    Rastogi, Namrata
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (13) : 1533 - 1537
  • [28] Enantioselective synthesis of P-stereogenic benzophospholanes via palladium-catalyzed intramolecular cyclization
    Brunker, Tim J.
    Anderson, Brian J.
    Blank, Natalia F.
    Glueck, David S.
    Rheingold, Arnold L.
    ORGANIC LETTERS, 2007, 9 (06) : 1109 - 1112
  • [29] Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1H)-ones
    Liu, Jian-Li
    Xu, Ren-Rui
    Wang, Wei
    Qi, Xinxin
    Wu, Xiao-Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (16) : 3584 - 3588
  • [30] A facile synthesis of indolo[3,2,1-jk]carbazoles via palladium-catalyzed intramolecular cyclization
    Lv, Jun
    Liu, Qiancai
    Tang, Jie
    Perdih, Franc
    Kranjc, Kristof
    TETRAHEDRON LETTERS, 2012, 53 (39) : 5248 - 5252