Synthesis of (E)-4,5-Dihydro-1H-Pyrazoles via Tandem Intermolecular Addition-Cyclization of N-Propargylic Sulfonylhydrazones

被引:0
|
作者
Tang, Hai-Tao
Zeng, Jia-Hao
Chen, Jun-Jia
Chen, Yi-Hui [1 ]
Zhan, Zhuang-Ping
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
propargyl hydrazones; dihydropyrazoles; acetals; intermolecular reaction; DIHYDROPYRAZOLE DERIVATIVES; SUBSTITUTED PYRAZOLES; ACCESS; ANNULATION; INHIBITORS; CASCADE; UTILITY; ESTERS; POTENT; AGENTS;
D O I
10.1055/s-0036-1588844
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the synthesis of (E)-4-benzylidene-4,5-dihydro-1H-pyrazoles through tandem intermolecular addition-intramolecular cyclization of N-propargylic sulfonylhydrazones has been developed. In this study, we firstly report that N-propargylic sulfonylhydrazones react with electrophilic reagents to afford 4-substituted pyrazole derivatives.
引用
收藏
页码:2036 / 2040
页数:5
相关论文
共 50 条
  • [1] Selective synthesis of 4-(sulfonyl)-methyl-1H-pyrazoles and (E)-4,5-dihydro-1H-pyrazoles from N-allenic sulfonylhydrazones
    Zhu, Yu
    Hong, Jun-Jie
    Zhou, Yun-Bin
    Xiao, Yu-Wei
    Lin, Min
    Zhan, Zhuang-Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (23) : 3797 - 3801
  • [2] N-(2-Vinyloxyethyl)-4,5-dihydro-1H-pyrazoles
    Kukharev, B. F.
    Stankevich, V. K.
    Lobanova, N. A.
    Klimenko, G. R.
    Sadykov, E. Kh.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (04) : 628 - 629
  • [3] N-(2-Vinyloxyethyl)-4,5-dihydro-1H-pyrazoles
    B. F. Kukharev
    V. K. Stankevich
    N. A. Lobanova
    G. R. Klimenko
    E. Kh. Sadykov
    Russian Journal of Organic Chemistry, 2007, 43 : 628 - 629
  • [4] Synthesis of 4,5-dihydro-1H-pyrazoles with chiral substituents at position 3 or 5
    Sviridova, L. A.
    Tavtorkin, A. N.
    Shalynina, N. A.
    Vorozhtsov, N. I.
    Protopopova, P. S.
    Urmambetova, Zh. S.
    Kochetkov, K. A.
    RUSSIAN CHEMICAL BULLETIN, 2015, 64 (05) : 1078 - 1082
  • [5] Synthesis of 4,5-dihydro-1H-pyrazoles with chiral substituents at position 3 or 5
    L. A. Sviridova
    A. N. Tavtorkin
    N. A. Shalynina
    N. I. Vorozhtsov
    P. S. Protopopova
    Zh. S. Urmambetova
    K. A. Kochetkov
    Russian Chemical Bulletin, 2015, 64 : 1078 - 1082
  • [6] A novel synthesis of 5-perfluorophenyl 4,5-dihydro-1H-pyrazoles in THF or water
    Pang, Wan
    Zhu, Shifa
    Jiang, Huanfeng
    Zhu, Shizheng
    JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (11) : 1379 - 1384
  • [7] Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics
    Marcos A. P. Martins
    Paulo H. Beck
    Lilian Buriol
    Clarissa P. Frizzo
    Dayse N. Moreira
    Mara R. B. Marzari
    Marcileia Zanatta
    Pablo Machado
    Nilo Zanatta
    Helio G. Bonacorso
    Monatshefte für Chemie - Chemical Monthly, 2013, 144 : 1043 - 1050
  • [8] Evaluation of the synthesis of 1-(pentafluorophenyl)-4,5-dihydro-1H-pyrazoles using green metrics
    Martins, Marcos A. P.
    Beck, Paulo H.
    Buriol, Lilian
    Frizzo, Clarissa P.
    Moreira, Dayse N.
    Marzari, Mara R. B.
    Zanatta, Marcileia
    Machado, Pablo
    Zanatta, Nilo
    Bonacorso, Helio G.
    MONATSHEFTE FUR CHEMIE, 2013, 144 (07): : 1043 - 1050
  • [9] Synthesis and structure of novel 4,5-dihydro-1H-pyrazoles:: salicylic acid based analgesic agents
    Machado, Pablo
    Rosa, Fernanda A.
    Rossatto, Marcelo
    Sant'Anna, Gabriela da S.
    Sauzem, Patricia D.
    da Silva, Rubia M. Siqueira
    Rubin, Maribel A.
    Ferreira, Juliano
    Bonacorso, Helio G.
    Zanatta, Nilo
    Martinsa, Marcos A. P.
    ARKIVOC, 2007, : 281 - 297
  • [10] ELECTRON-IMPACT MASS-SPECTROMETRY OF TRIFLUOROMETHYL-SUBSTITUTED 4,5-DIHYDRO-1H-PYRAZOLES AND 4,5-DIHYDRO-3H-PYRAZOLES
    DILIDDO, D
    BRUCHE, L
    BRAVO, P
    FAVRETTO, D
    TRALDI, P
    GAZZETTA CHIMICA ITALIANA, 1992, 122 (10): : 397 - 402