Copper-Catalyzed Cycloaddition/Coupling Cascades of Azomethine Imines with Alkynes for Divergent Synthesis of (Z)-Alkenyl and Alkynyl N,N′-Bicyclic Pyrazolidinones

被引:1
|
作者
Jiang, Wei [1 ]
Sun, Bo-Xun [1 ]
Fan, Tai-Gang [1 ]
Zhang, Cui [1 ]
Zhou, Xin-Song [1 ]
Shen, Yuehai [1 ]
Li, Ya-Min [1 ]
机构
[1] Kunming Univ Sci & Technol, Fac Life Sci & Technol, Kunming 650500, Peoples R China
基金
中国国家自然科学基金;
关键词
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; ANTIBACTERIAL AGENTS; CLICK CHEMISTRY; METAL; ALKENES; AMINES; SERIES; AZIDES;
D O I
10.1021/acs.orglett.4c03824
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed cycloaddition/coupling cascades utilizing azomethine imines and alkynes have been developed for the divergent synthesis of (Z)-alkenyl and alkynyl N,N '-bicyclic pyrazolidinones by varying the reaction conditions. The choice of inert or oxidative atmosphere plays a crucial role in determining the transformation pathways. These reactions have broad substrate scopes and mild conditions, making them potentially useful.
引用
收藏
页码:11090 / 11095
页数:6
相关论文
共 50 条
  • [41] Copper-Catalyzed Oxidative Coupling of Carboxylic Acids with N,N-Dialkylformamides: An Approach to the Synthesis of Amides (pg 1218, 2013)
    Kumar, P. Santhosh
    Kumar, G. Sathish
    Kumar, R. Arun
    Reddy, N. Veera
    Reddy, K. Rajender
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (14) : 2941 - 2941
  • [42] Synthesis of N-1-aryl-purine nucleosides using copper-catalyzed C-N coupling of boronic acids
    Strouse, JJR
    Jeselnik, M
    Arterburn, JB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U187 - U187
  • [43] Synthesis of α-Ketoamides from Aryl Methyl Ketones and N,N-Dimethylformamide via Copper-Catalyzed Aerobic Oxidative Coupling
    Zhou, Mingxin
    Song, Qiuling
    SYNTHESIS-STUTTGART, 2014, 46 (14): : 1853 - 1858
  • [44] Microwave-Assisted Copper-Catalyzed Coupling of Bromoalkynes and Sulfonamides: Rapid Synthesis of N -Sulfonyl Ynamides
    Hong, Su Jeong
    Lee, Joon-Ho
    Yeom, Hyun-Suk
    SYNLETT, 2024, 35 (12) : 1436 - 1440
  • [45] The synthesis of arylcyanamides: a copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy
    Boddapati, S. N. Murthy
    Polam, Naresh
    Mutchu, Baby Ramana
    Bollikolla, Hari Babu
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (02) : 918 - 922
  • [46] Copper-catalyzed three component C-S/C-N coupling for the synthesis of trifluorothioacetamides
    Hu, Bo-Lun
    Song, Yi-Kang
    Zhang, Guoqiang
    Yao, Zengwen
    Zhang, Xing-Guo
    JOURNAL OF FLUORINE CHEMISTRY, 2020, 239
  • [47] Copper-Catalyzed Chemoselective Coupling of N-Dithiophthalimides and Alkyl Halides: Synthesis of Unsymmetrical Disulfides and Sulfides
    Li, Bin
    Liu, Bo-Xi
    Rao, Weidong
    Shen, Shu-Su
    Sheng, Daopeng
    Wang, Shun-Yi
    ORGANIC LETTERS, 2024, 26 (17) : 3634 - 3639
  • [48] Copper-Catalyzed One-Pot Synthesis of N-Sulfonylalkanimidoyl Thiocyanates from Sulfonyl Azides, Alkynes, and KSCN
    Yavari, Issa
    Damghani, Tahereh
    Nematpour, Manijeh
    HELVETICA CHIMICA ACTA, 2013, 96 (12) : 2214 - 2217
  • [49] Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes
    Jin, T
    Kamijo, S
    Yamamoto, Y
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (18) : 3789 - 3791
  • [50] Copper-Catalyzed Tandem Azide-Alkyne Cycloaddition, Ullmann Type C-N Coupling, and Intramolecular Direct Arylation
    Pericherla, Kasiviswanadharaju
    Jha, Amitabh
    Khungar, Bharti
    Kumar, Anil
    ORGANIC LETTERS, 2013, 15 (17) : 4304 - 4307