Synthesis of 2,3-Ring Fused Pyrroles via Cu-Catalyzed 5-exo-dig Annulation of Alkyne-Tethered Enaminones

被引:9
|
作者
Li, Weishuang [1 ,2 ]
Usman, Muhammad [1 ,2 ]
Wu, Lin-Yang [1 ,2 ]
Liu, Wen-Bo [1 ,2 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Engn Res Ctr Organosilicon Cpds & Mat, Minist Educ, Wuhan 430072, Hubei, Peoples R China
[2] Wuhan Univ, Sauvage Ctr Mol Sci, Wuhan 430072, Hubei, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 23期
关键词
POLYSUBSTITUTED PYRROLES; EFFICIENT SYNTHESIS; CYCLIZATION; HYDROAMINATION; DERIVATIVES; AMINES; INDOLES;
D O I
10.1021/acs.joc.9b02672
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed annulation of alkyne-tethered enaminones for the synthesis of 2,3-ring fused pyrroles is reported. The S-exo-dig cyclization/olefin migration reaction delivers the multisubstituted pyrroles in 59-99% yields with 16 examples. This strategy features easily available starting materials, mild reaction conditions, and a cheap ligand-free copper catalyst. The atom-economic transformation provides a simple access to a variety of synthetic useful pyrroles and their derivatives.
引用
收藏
页码:15754 / 15763
页数:10
相关论文
共 13 条
  • [1] Enantioselective Synthesis of Fused Isocoumarins via Palladium-Catalyzed Annulation of Alkyne-Tethered Malononitriles
    Zhang, Hui
    Li, Weishuang
    Hu, Xu-Dong
    Liu, Wen-Bo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15): : 10799 - 10811
  • [2] Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls
    Chernyak, Natalia
    Gevorgyan, Vladimir
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) : 1101 - 1114
  • [3] Palladium Catalyzed, Multicomponent Synthesis of Fused-Ring Pyrroles from Aryl Iodides, Carbon Monoxide, and Alkyne-Tethered Imines
    Firoozi, Neda
    Torres, Gerardo M.
    Arndtsen, Bruce A.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11145 - 11152
  • [4] Stereoselective tandem synthesis of oxazolo-fused pyrroloquinolines from o-alkynylaldehydes via Ag(I)-catalyzed regioselective 5-exo-dig ring closure
    Jha, Rajeev Ranjan
    Aggarwal, Trapti
    Verma, Akhilesh Kumar
    [J]. TETRAHEDRON LETTERS, 2014, 55 (16) : 2603 - 2608
  • [5] Regioselective synthesis of phthalans via Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohols
    Praveen, Chandrasekaran
    Iyyappan, Chandran
    Perumal, Paramasivan Thirumalai
    [J]. TETRAHEDRON LETTERS, 2010, 51 (36) : 4767 - 4771
  • [6] Palladium-Catalyzed [2+2+1] Annulation of Alkyne-Tethered Aryl Iodides with Diaziridinone: Synthesis of 3,4-Fused Tricyclic Indoles
    Zhang, Lei
    Chen, Junyu
    Zhong, Tianshuo
    Zheng, Xiangyun
    Zhou, Jian
    Jiang, Xinpeng
    Yu, Chuanming
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 10823 - 10834
  • [7] Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy
    He, Xinwei
    Wang, Demao
    Liu, Yanan
    Wu, Mengdi
    Kong, Yangzilin
    Tang, Qiang
    Wang, Yiping
    Fan, Chenli
    Shang, Yongjia
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (46) : 9159 - 9172
  • [8] [Cu]-Catalyzed Domino Sonogashira Coupling Followed by Intramolecular 5-exo-dig Cyclization: Synthesis of 1,3-Dihydro-2-benzofurans
    Mahendar, Lodi
    Reddy, Alavala Gopi Krishna
    Krishna, Jonnada
    Satyanarayana, Gedu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18): : 8566 - 8576
  • [9] Cu-Catalyzed Radical Cascade Annulations of Alkyne-Tethered N-Alkoxyamides with Air: Facile Access to Isoxazolidine/1,2-Oxazinane-Fused Isoquinolin-1(2H)-ones
    Chen, Fei
    Lai, Sheng-Qiang
    Zhu, Fei-Fei
    Meng, Qiang
    Jiang, Yu
    Yu, Wei
    Han, Bing
    [J]. ACS CATALYSIS, 2018, 8 (09): : 8925 - 8931
  • [10] One-pot Selective Synthesis of 2,3-Dihydro-4H-Furo[3,2-c] coumarins by Palladium-Catalyzed Silver-Assisted Propargylation/Intramolecular 5-exo-dig Cyclization
    Uchiyama, Chihiro
    Miyadera, Yukari
    Hayashi, Yoshio
    Yakushiji, Fumika
    [J]. CHEMISTRYSELECT, 2017, 2 (13): : 3794 - 3798