Cs2CO3-Promoted [3+2] Cyclization of Chalcone and N-Tosylhydrazone

被引:0
|
作者
He, Jing [1 ]
Liu, Yali [1 ]
Feng, Yijiao [1 ]
Li, Xuezhen [1 ]
Liu, Ping [1 ]
Dai, Bin [1 ]
机构
[1] Shihezi Univ, Sch Chem & Chem Engn, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832004, Peoples R China
基金
中国国家自然科学基金;
关键词
Chalcone; cyclization; N-tosylhydrazone; FULLY SUBSTITUTED PYRAZOLES; TRANSITION-METAL; 3-COMPONENT REACTION; EFFICIENT; FUNCTIONALIZATION; CONSTRUCTION; HYDRAZINES; ALDEHYDES;
D O I
10.1080/10406638.2022.2078845
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cs2CO3-promoted [3 + 2] cyclization of chalcone and N-tosylhydrazones has been developed, a series of novel (4,5-diaryl-1H-pyrazol-3-yl)(aryl)methanone derivatives were synthesized with a wide range of substrates, good tolerance of functional groups and by a one-pot three-component reaction of chalcone, aryl formaldehyde, and TsNHNH2. In addition, the gram-scale synthesis of the product and further transformations were also investigated.
引用
收藏
页码:3827 / 3839
页数:13
相关论文
共 50 条
  • [31] I2-Promoted [3+2] Cyclization of Thiocarbamates with Enaminones: a Protocol for the Synthesis of Polysubstituted Thiazol-2(3H)-ones
    Xu, Xiao-Hu
    Weng, Jia-Hao
    Chen, Yi
    Dong, Zhi-Bing
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (07) : 1649 - 1653
  • [32] Cs2CO3-Promoted C-O Coupling Protocol Enables Solventless (Hetero)aryl Ether Synthesis under Air Atmosphere
    Jiang, Bowen
    Chen, Cheng
    Fan, Guang-Gao
    Sang, Wei
    Cheng, Hua
    Zhang, Rui
    Yuan, Ye
    Li, Qi-Zhong
    Verpoort, Francis
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (06)
  • [33] Silver-Promoted Rapid Synthesis of 3-Arylindan-1-ones: Microwave-Assisted Reductive Coupling of N-Tosylhydrazone and Boronic Acids
    Tamizharasan, Natarajan
    Santhoshkumar, Pandeeswaran
    Devarajan, Nainamalai
    Hallur, Mahanandeesha S.
    Hallur, Gurulingappa
    Suresh, Palaniswamy
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7417 - 7428
  • [34] The Reaction of o-Aminoacetophenone N-Tosylhydrazone and CO2 toward 1,4-Dihydro-2H-3,1-benzoxazin-2-ones
    Xiong, Hao
    Wu, Xiaopeng
    Wang, Hepan
    Sun, Song
    Yu, Jin-Tao
    Cheng, Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (15) : 3538 - 3542
  • [35] [3+2] Cyclization of Difluoroacetohydrazonoyl Bromides with β-(N,N-Dimethylamino)enones/Enoates/Enamides
    Li Xiaoyong
    Huang Danfeng
    Zhou Yuxiu
    Liu Xiaokang
    Wang Kehu
    Wang Junjiao
    Hu Yulai
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1226 - 1239
  • [36] Remarkable temperature effect on intramolecular [3+2] cyclization
    Gromov, Alexey
    Enev, Valentin
    Mulzer, Johann
    TETRAHEDRON LETTERS, 2009, 50 (37) : 5283 - 5284
  • [37] A [3+2] Cyclization of Siloxyalkynes and Isocyanides for the Synthesis of Oxazoles
    Wu, An
    Sun, Jianwei
    SYNLETT, 2019, 30 (04) : 515 - 518
  • [38] Phosphine catalyzed [3+2] cyclization/Michael addition of allenoate with CS2 to form 2-thineyl vinyl sulfide
    Fei, Weihong
    Xu, Ping
    Hou, Jie
    Yao, Weijun
    CHEMICAL COMMUNICATIONS, 2020, 56 (78) : 11669 - 11672
  • [39] Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides
    Zhao Yu
    Liu Xinlei
    Wang Weiwei
    Geng Rui
    Wang, Mingan
    SYNTHESIS-STUTTGART, 2018, 50 (20): : 4055 - 4062
  • [40] A copper(II) perchlorate-promoted tandem reaction of internal alkynol and salicyl N-tosylhydrazone: direct access to isochromeno[3,4-b]chromene
    Siyang, Hai Xiao
    Wu, Xu Rui
    Ji, Xiao Yue
    Wu, Xin Yan
    Liu, Pei Nian
    CHEMICAL COMMUNICATIONS, 2014, 50 (62) : 8514 - 8517