Facile construction of benzofulvene frameworks via a palladium-catalysed three-component reaction

被引:0
|
作者
Zhu, Bo [1 ,2 ]
Chen, Zhi-Chao [1 ,2 ]
Du, Wei [1 ,2 ]
Chen, Ying-Chun [1 ,2 ,3 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst, Minist Educ, Chengdu 610041, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Sichuan Res Ctr Drug Precis Ind Technol, Chengdu 610041, Peoples R China
[3] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China
基金
中国国家自然科学基金;
关键词
BIOLOGICAL EVALUATION; INHIBITORS; LIGANDS; 1,3-ENYNES; 1,3-DIENES; ANNULATION; SULINDAC;
D O I
10.1039/d4ob01414f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here we report a three-component reaction of 2-formylarylboronic acids, N-sulfonyl amines and 1,3-enynes, proceeding through a cascade imine formation/Pd-0-catalysed vinylogous addition/intramolecular Suzuki coupling/isomerization process. This protocol exhibited broad substrate scope and good functionality tolerance, and a spectrum of multifunctionalised benzofulvene derivatives were furnished in moderate to good yields and E/Z-selectivity.
引用
收藏
页码:8397 / 8400
页数:4
相关论文
共 50 条
  • [1] Domino allylic amination/Sonogashira/heterocyclisation reactions: palladium-catalysed three-component synthesis of pyrroles
    Lamande-Langle, Sandrine
    Abarbri, Mohamed
    Thibonnet, Jerome
    Duchene, Alain
    Parrain, Jean-Luc
    CHEMICAL COMMUNICATIONS, 2010, 46 (28) : 5157 - 5159
  • [2] Palladium-catalysed construction of butafulvenes
    Huang, Xin
    Chen, Bing-Zhi
    Li, Pengbin
    Ji, Ding-Wei
    Liu, Jinxian
    Zheng, Hao
    Yang, Sa-Na
    Hu, Yan-Cheng
    Wan, Boshun
    Hu, Xiang-Ping
    Fu, Chunling
    Huang, Yankai
    Zheng, Jian
    Chen, Qing-An
    Ma, Shengming
    NATURE CHEMISTRY, 2022, 14 (10) : 1185 - +
  • [3] Palladium-catalysed construction of butafulvenes
    Xin Huang
    Bing-Zhi Chen
    Pengbin Li
    Ding-Wei Ji
    Jinxian Liu
    Hao Zheng
    Sa-Na Yang
    Yan-Cheng Hu
    Boshun Wan
    Xiang-Ping Hu
    Chunling Fu
    Yankai Huang
    Jian Zheng
    Qing-An Chen
    Shengming Ma
    Nature Chemistry, 2022, 14 : 1185 - 1192
  • [4] Palladium-catalysed three component synthesis of α,β-unsaturated amidines and imidates
    Kishore, K
    Tetala, R
    Whitby, RJ
    Light, ME
    Hurtshouse, MB
    TETRAHEDRON LETTERS, 2004, 45 (38) : 6991 - 6994
  • [5] Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction
    He, Yu-Wei
    Huang, Li
    Huang, Kun
    Yan, Chao-Guo
    Sun, Jing
    Han, Ying
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15): : 10854 - 10866
  • [6] One-pot three-component sulfone synthesis exploiting palladium-catalysed aryl halide aminosulfonylation
    Richards-Taylor, Charlotte S.
    Blakemore, David C.
    Willis, Michael C.
    CHEMICAL SCIENCE, 2014, 5 (01) : 222 - 228
  • [7] Palladium catalysed, three-component cascade reaction for the efficient synthesis of diverse small molecules
    Herbert, Jack
    Edwards, Kelsey
    Sridharan, Visuvanathar
    TETRAHEDRON LETTERS, 2020, 61 (46)
  • [8] Straightforward three-component palladium-catalysed synthesis of pyridazin-3(2H)-one libraries
    Coelho, A
    Sotelo, E
    COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2006, 9 (01) : 15 - 19
  • [9] Facile synthesis of primary amides and ketoamides via a palladium-catalysed carbonylation-deprotection reaction sequence
    Takacs, Eszter
    Varga, Csilla
    Skoda-Foldes, Rita
    Kollar, Laszlo
    TETRAHEDRON LETTERS, 2007, 48 (14) : 2453 - 2456
  • [10] Synthesis of Indenes and Benzofulvenes via a Palladium-Catalyzed Three-Component Reaction
    Abel-Snape, Xavier
    Wycich, Gina
    Lautens, Mark
    ACS CATALYSIS, 2022, 12 (06) : 3291 - 3301