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
  • [1] Synthesis of thiophene derivatives via palladium-catalyzed coupling reactions
    Arai, Nobumichi
    Miyaoku, Takayuki
    Teruya, Shota
    Mori, Atsunori
    TETRAHEDRON LETTERS, 2008, 49 (06) : 1000 - 1003
  • [2] Synthesis of ikimine a via palladium-catalyzed coupling
    Larock, RC
    Dong, XY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 288 - ORGN
  • [3] Synthesis of indene and naphthalene derivatives by a palladium-catalyzed domino carbopalladation/cyclization/coupling process
    Guo, Li-Na
    Duan, Xin-Hua
    Hu, Jie
    Bi, Hai-Peng
    Liu, Xue-Yuan
    Liang, Yong-Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (08) : 1418 - 1425
  • [4] Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives
    Burger, Erin C.
    Tunge, Jon A.
    Journal of the American Chemical Society, 2006, 128 (31): : 10002 - 10003
  • [5] Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives
    Burger, Erin C.
    Tunge, Jon A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) : 10002 - 10003
  • [6] SYNTHESIS OF ANTHRAQUINONE DERIVATIVES BY PALLADIUM-CATALYZED COUPLING OF TRIFLATES WITH STANNANES
    TAMAYO, N
    ECHAVARREN, AM
    PAREDES, MC
    FARINA, F
    NOHEDA, P
    TETRAHEDRON LETTERS, 1990, 31 (36) : 5189 - 5192
  • [7] An efficient synthesis of 4-substituted coumarin derivatives via a palladium-catalyzed Suzuki cross-coupling reaction
    Rajale, Trideep
    Sharma, Shikha
    Stroud, Daniel A.
    Unruh, Daniel K.
    Miaou, Emily
    Lai, Kimberly
    Birney, David M.
    TETRAHEDRON LETTERS, 2014, 55 (49) : 6627 - 6630
  • [8] Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation
    Geng, Xin
    He, Heng
    Shatskiy, Andrey
    Stepanova, Elena V.
    Alvey, Gregory R.
    Liu, Jian-Quan
    Karkas, Markus D.
    Wang, Xiang-Shan
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12738 - 12743
  • [9] Biaryl synthesis via palladium-catalyzed aryne multicomponent coupling
    Henderson, Jaclyn L.
    Edwards, Andrew S.
    Greaney, Michael F.
    ORGANIC LETTERS, 2007, 9 (26) : 5589 - 5592
  • [10] Palladium-Catalyzed Synthesis of Conjugated Allenynes via Decarboxylative Coupling
    Smith, Mary K.
    Tunge, Jon A.
    ORGANIC LETTERS, 2017, 19 (20) : 5497 - 5500