Synthesis of phenanthridinones using Cu- or Pd-mediated C-N bond formation

被引:11
|
作者
Nealmongkol, Prattya [1 ]
Calmes, Jordan [2 ]
Ruchirawat, Somsak [1 ,2 ,3 ]
Thasana, Nopporn [1 ,2 ,3 ]
机构
[1] Chulabhorn Grad Inst, Chem Biol Program, Kamphaeng Phet 6, Bangkok 10210, Thailand
[2] Chulabhorn Res Inst, Med Chem Lab, Kamphaeng Phet 6, Bangkok 6, Thailand
[3] Minist Educ, CHE, Ctr Excellence Environm Hlth & Toxicol, Bangkok 10210, Thailand
关键词
Copper; Palladium; C-N bond formation; Phenanthridinone; Lactam; BIARYL SYNTHESIS; H ACTIVATION; AROMATIC CARBOXYLATES; LAMELLARIN ALKALOIDS; EFFICIENT SYNTHESIS; COUPLING REACTION; ACIDS; ANNULATION; AMIDATION; AMINATION;
D O I
10.1016/j.tet.2016.12.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chemoselective synthesis of phenanthridinones was studied using copper(I)-and palladium(II)-catalyzed C-N bond formation with various bases, ligands, and solvents. Phenanthridinones were obtained from 2-halobiarylcarboxylates and amines in a one-pot reaction. The phenanthridinones and heterocyclic-fused lactam derivatives were accomplished using developed methods. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:735 / 741
页数:7
相关论文
共 50 条
  • [1] Synthesis of benzoindoloquinolizines via a Cu(I)-mediated C-N bond formation
    Worayuthakarn, Rattana
    Nealmongkol, Prattya
    Ruchirawat, Somsak
    Thasana, Nopporn
    TETRAHEDRON, 2012, 68 (13) : 2864 - 2875
  • [2] Synthesis of azanovobiocin derivatives using Cu(I)/Pd(II)-catalyzed C-N bond formation
    Moss, Steven M.
    Nealmongkol, Prattya
    Thasana, Nopporn
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [3] Pd-mediated P-C bond formation.
    Zhuravel, MA
    Sweeder, RD
    Glueck, DS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U26 - U26
  • [4] Synthesis of Diversely Substituted Indoloquinolinones via Pd(II)/Cu(II)-Mediated Oxidative C-C Bond Formation and I(III)-Mediated C-N Bond Formation
    Zhang, Xiang
    Zhang-Negrerie, Daisy
    Deng, Jun
    Du, Yunfei
    Zhao, Kang
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (24): : 12750 - 12759
  • [5] Stable Pd-nanoparticles catalyzed domino C-H activation/C-N bond formation strategy: An access to phenanthridinones
    Saha, Rajib
    Sekar, Govindasamy
    JOURNAL OF CATALYSIS, 2018, 366 : 176 - 188
  • [6] Iron Mediated Desulfurization and C-N Bond Formation: Strategy for the Synthesis of Thioureas
    Pendem, Venkata Bhavanarushi
    Nannapaneni, Madhavi
    LETTERS IN ORGANIC CHEMISTRY, 2018, 15 (12) : 1025 - 1029
  • [7] Pd-Catalyzed C-N bond formation: Applications to the synthesis of a drug candidate
    Huang, Jinkun
    Chen, Ying
    King, Anthony
    Wang, Xin
    Wang, Xiang
    Bunel, Emilio
    Larsen, Robert D.
    Faul, Margaret M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [8] Synthesis of polymers containing C-N bond using Pd-catalyst
    Shan, Wenwen
    Zhu, Fanghua
    Zhang, Lin
    MATERIALS AND COMPUTATIONAL MECHANICS, PTS 1-3, 2012, 117-119 : 1207 - +
  • [9] Easy Access to Phenanthridinones via Metal-Free Cascade Benzannulation and C-N Bond Formation
    Preeti, Kailas V.
    Kallurkar, Kailas V.
    Mainkar, Prathama S.
    Adepu, Raju
    Chandrasekhar, Srivari
    ORGANIC LETTERS, 2023, 25 (47) : 8408 - 8412
  • [10] Iminoiodanes and C-N bond formation in organic synthesis
    Dauban, P
    Dodd, RH
    SYNLETT, 2003, (11) : 1571 - 1586