Silver(I)-Catalyzed Conia-Ene Reaction: Synthesis of 3-Pyrrolines via a 5-endo-dig Cyclization

被引:32
|
作者
Boominathan, Siva Senthil Kumar [1 ]
Hu, Wan-Ping [2 ]
Senadi, Gopal Chandru [1 ]
Wang, Jeh-Jeng [1 ]
机构
[1] Kaohsiung Med Univ, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
[2] Kaohsiung Med Univ, Dept Biotechnol, Kaohsiung 807, Taiwan
关键词
alkynes; Conia-ene reaction; 2-pyrroles; 3-pyrrolines; silver; 1,3-DIPOLAR CYCLOADDITION; 1,3-DICARBONYL COMPOUNDS; CLOSING METATHESIS; BETA-KETOESTERS; GOLD CATALYSIS; TRIFLIC ACID; ALKYNES; INHIBITORS; HETEROCYCLES; PYRROLIDINE;
D O I
10.1002/adsc.201300844
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel method has been developed for the synthesis of 3-pyrrolines from -ketopropargylamines via a 5-endo-dig carbocyclization. This transformation involves a silver-catalyzed Conia-ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2-substituted pyrroles under base-mediated conditions.
引用
收藏
页码:3570 / 3574
页数:5
相关论文
共 50 条
  • [41] Functionalized Benzofurans via Microwave-Promoted Tandem Claisen-Rearrangement/5-endo-dig Cyclization
    Schultze, Christiane
    Schmidt, Bernd
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (09) : 2619 - 2629
  • [42] Synthesis of Spiro[4.5]ecanes by Au(I)-Catalyzed Vinylogous Conia Ene Reaction
    Liu, Fuhai
    Ruan, Zhongting
    Duan, Xiaoguang
    Ma, Ruize
    Su, Xujuan
    Liang, Ning
    Xie, Xingang
    She, Xuegong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (04)
  • [43] Gold(I)-Promoted Heterocyclization of Internal Alkynes: A Comparative Study of Direct Metallate 5-endo-dig Cyclization versus a Stepwise Cyclization
    French, Jonathan M.
    Diver, Steven T.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5569 - 5585
  • [44] Asymmetric cyclizations via a sequential Michael addition/Conia-ene reaction by combining multifunctional quaternary phosphonium salt and silver catalysis
    Fang, Guosheng
    Zheng, Changwu
    Cao, Dongdong
    Pan, Lu
    Hong, Haoran
    Wang, Hongyu
    Zhao, Gang
    TETRAHEDRON, 2019, 75 (18) : 2706 - 2716
  • [45] Yb(OTf)3-Promoted ZnCl2-Catalyzed Conia-Ene Reaction of Linear β-Alkynic β-Dicarbonyls
    Liu, Yu
    Song, Ren-Jie
    Li, Jin-Heng
    SYNTHESIS-STUTTGART, 2010, (21): : 3663 - 3669
  • [46] Synthesis of Substituted Naphtho-Ferrocenes via a Gold(I)-Catalyzed Intramolecular 6-endo-Dig Cyclization
    Zhang, Pei-Chao
    Wang, Yidong
    Qian, Deyun
    Li, Wenbo
    Zhang, Junliang
    CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (06) : 849 - 852
  • [47] Lithium Enables Pd-Catalyzed 5-endo-dig Cyclization/Coupling of α-Homopropargyl-β-ketoesters with Aryl Bromides and Triflates
    Bisek, Bartosz
    Kochaniak, Katarzyna
    Chaladaj, Wojciech
    ORGANIC LETTERS, 2024, 26 (39) : 8254 - 8259
  • [48] One-Pot Tandem Michael Addition/Enantioselective Conia-Ene Cyclization Mediated by Chiral Iron(III)/Silver(I) Cooperative Catalysis
    Horibe, Takahiro
    Sakakibara, Masato
    Hiramatsu, Rin
    Takeda, Kazuki
    Ishihara, Kazuaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (38) : 16470 - 16474
  • [49] A sequential Ugi-Smiles/transition-metal-free endo-dig Conia-ene cyclization: the selective synthesis of saccharin substituted 2,5-dihydropyrroles (vol 45, pg 15647, 2021)
    Seyrani, Hassan
    Ramezanpour, Sorour
    Vaezghaemi, Aref
    Kobarfard, Farzad
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (46) : 21577 - 21577
  • [50] Synthesis of 3-Halo-7-azaindoles through a 5-endo -dig Electrophilic Cyclization Reaction
    Philips, Aimee
    Cunningham, Christopher
    Naran, Kajal
    Kesharwani, Tanay
    SYNLETT, 2019, 30 (10) : 1246 - 1252