Efficient synthesis of phenanthridinone derivatives via a palladium-catalyzed coupling process

被引:76
|
作者
Furuta, Takumi [1 ]
Kitamura, Yuki [1 ]
Hashimoto, Ayano [1 ]
Fujii, Satoshi [1 ]
Tanaka, Kiyoshi [1 ]
Kan, Toshiyuki [1 ]
机构
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
关键词
D O I
10.1021/ol062599z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-mediated domino reaction was developed to conveniently synthesize phenanthridinone derivatives. Phosphine ligand 1 strongly promotes the domino process, which includes aryl-aryl coupling and C-N bond formations concomitant with a deamidation reaction. The versatility and applicability to a broad range of substrates make this reaction useful for the development of bioactive derivatives.
引用
收藏
页码:183 / 186
页数:4
相关论文
共 50 条
  • [21] Synthesis of tryptophan derivatives via a palladium-catalyzed N-heteroannulation
    Dacko, Christopher A.
    Akhmedov, Novruz G.
    Soderberg, Bjorn C. G.
    TETRAHEDRON-ASYMMETRY, 2008, 19 (24) : 2775 - 2783
  • [22] Palladium-catalyzed enantioselective synthesis of cyclohexene derivatives via kinetic resolution
    Nishimata, T
    Yamaguchi, K
    Mori, M
    TETRAHEDRON LETTERS, 1999, 40 (31) : 5713 - 5716
  • [24] Synthesis of pyridinylpyrrole derivatives via the palladium-catalyzed reaction of acetylpyridines with methyleneaziridines
    Siriwardana, AI
    Kathriarachchi, KKADS
    Nakamura, I
    Gridnev, ID
    Yamamoto, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) : 13898 - 13899
  • [25] Palladium-catalyzed highly efficient synthesis of functionalized indolizines via cross-coupling/cycloisomerization cascade
    Zhang, Liangwei
    Li, Xiangdong
    Liu, Yuanhong
    Zhang, Dayong
    CHEMICAL COMMUNICATIONS, 2015, 51 (30) : 6633 - 6636
  • [26] The asymmetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds
    Cho, SY
    Shibasaki, M
    TETRAHEDRON-ASYMMETRY, 1998, 9 (21) : 3751 - 3754
  • [27] SYNTHESIS OF PYRIDINE ALKALOIDS BY PALLADIUM-CATALYZED COUPLING
    WANG, Y
    LAROCK, RC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 353 - ORGN
  • [28] The use of polysaccharides and derivatives in palladium-catalyzed coupling reactions
    Molnar, Arpad
    Papp, Attila
    CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (02) : 295 - 310
  • [29] Synthesis of aryl-substituted indanones and indenes via a highly efficient ligand-free palladium-catalyzed Suzuki coupling process
    Song, Yuming
    Xie, Yamei
    Chen, Minjian
    Qu, Jingping
    Hu, Hongfan
    Lang, Xiaomei
    Xue, Shan
    Ran, Yin
    Xin, Shixuan
    ARKIVOC, 2016, : 306 - 327
  • [30] A NEW PALLADIUM-CATALYZED SYNTHESIS OF INDOXYL DERIVATIVES
    AN, ZW
    CATELLANI, M
    CHIUSOLI, GP
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 397 (02) : C31 - C32