A novel synthesis of 5-perfluorophenyl 4,5-dihydro-1H-pyrazoles in THF or water

被引:4
|
作者
Pang, Wan
Zhu, Shifa
Jiang, Huanfeng
Zhu, Shizheng [1 ]
机构
[1] S China Univ Technol, Coll Chem, Guangzhou 510640, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
perfluorobenyl; pyrazoles; alpha; beta-unsaturated carbonyl compounds; water;
D O I
10.1016/j.jfluchem.2007.06.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
5-Perfluorophenyl 4,5-dihydro-1H-pyrazoles were synthesized from 1,3-dipolar cycloaddition reaction of perfluorobenyl 2,4,6-triisopropyl-benzenesulfonylhydrazone and alpha,beta-unsaturated carbonyl compounds or acrylonitrile in THF or water. It was worthy to note that better results were obtained when water was employed as the solvent, which was considered as an effective, economic and environmentally friendly method to synthesize these pyrazole derivatives. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:1379 / 1384
页数:6
相关论文
共 50 条
  • [11] 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
  • [12] Antipyretic and antioxidant activities of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles in rats
    Pasin, J. S. M.
    Ferreira, A. P. O.
    Saraiva, A. L. L.
    Ratzlaff, V.
    Andrighetto, R.
    Machado, P.
    Marchesan, S.
    Zanette, R. A.
    Bonacorso, H. G.
    Zanatta, N.
    Martins, M. A. P.
    Ferreira, J.
    Mello, C. F.
    BRAZILIAN JOURNAL OF MEDICAL AND BIOLOGICAL RESEARCH, 2010, 43 (12) : 1193 - 1202
  • [13] 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
  • [14] Activity of 4,5-dihydro-1H-pyrazoles against Mycobacterium tuberculosis and nontuberculous mycobacteria
    Ramos, Daniela Fernandes
    Fiss, Gabriela
    Frizzo, Clarissa Piccinin
    Pinto Martins, Marcos Antonio
    Bonacorso, Helio Gauze
    Zanatta, Nili
    Almeida da Silva, Pedro Eduardo
    INTERNATIONAL JOURNAL OF ANTIMICROBIAL AGENTS, 2014, 43 (05) : 481 - 483
  • [15] Dehydrozingerone based 1-acetyl-5-aryl-4,5-dihydro-1H-pyrazoles: Synthesis, characterization and anticancer activity
    Ratkovic, Zoran
    Muskinja, Jovana
    Burmudzija, Adrijana
    Rankovic, Branislav
    Kosanic, Marijana
    Bogdanovic, Goran A.
    Markovic, Bojana Simovic
    Nikolic, Aleksandar
    Arsenijevic, Nebojsa
    Dordevic, Snezana
    Vukicevic, Rastko D.
    JOURNAL OF MOLECULAR STRUCTURE, 2016, 1109 : 82 - 88
  • [16] Reactions of vinyl 2,3-epoxypropyl ethers with 4,5-dihydro-1H-pyrazoles
    B. F. Kukharev
    V. K. Stankevich
    N. A. Lobanova
    V. G. Chernova
    E. Kh. Sadykov
    V. A. Apkhanov
    Russian Journal of Organic Chemistry, 2006, 42 : 1498 - 1500
  • [17] 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
  • [18] Chiral induction in 1,3-dipolar cycloadditions: Preparation of 4,5-dihydro-1H-pyrazoles
    Pruitt, James R.
    Callmann, Cassandra E.
    Gauthier, Zoe H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [19] Reactions of vinyl 2,3-epoxypropyl ethers with 4,5-dihydro-1H-pyrazoles
    Kukharev, B. R.
    Stankevich, V. K.
    Lobanova, N. A.
    Chernova, V. G.
    Sadykov, E. Kh.
    Apkhanov, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (10) : 1498 - 1500
  • [20] One-pot synthesis of 5-fluoroalkyl-5-hydroxy-4-hydroxy-imino-1-isonicotinoyl-4,5-dihydro-1H-pyrazoles and their tuberculostatic activity
    Khudina, O. G.
    Burgart, Ya. V.
    Saloutin, V. I.
    Kravchenko, M. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (06) : 904 - 909