Regiospecific preparation of 1,4,5-trisubstituted pyrazoles from 2-(1H-1,2,3-benzotriazol-1-yl)-3-(4-aryl)-2-propenals

被引:15
|
作者
Katritzky, Alan R. [1 ]
Vakulenko, Anatoliy V. [1 ]
Akue-Gedu, Rufine [1 ]
Gromova, Anna V. [1 ]
Witek, Rachel [1 ]
Rogers, James W. [1 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Compounds, Gainesville, FL 32611 USA
关键词
pyrazoles; regiospecific synthesis; cyclization reaction;
D O I
10.3998/ark.5550190.0008.102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of alpha-benzotriazolyl-alpha,beta-unsaturated aldehydes with monosubstituted hydrazines followed by alkylation at the 4- position of the pyrazoline ring and elimination of the benzotriazole group affords 1,4,5- trisubstituted pyrazoles in overall yields of 52 - 79%.
引用
收藏
页码:9 / 21
页数:13
相关论文
共 50 条
  • [41] Synthesis and Activity Evaluation of 2-(1-naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles
    Kumaraswamy, M. N.
    Chandrashekhar, C.
    Shivakumar, H.
    Mathias, D. A. Prathima
    Mahadevan, K. M.
    Vaidya, V. P.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2008, 70 (06) : 715 - 720
  • [42] Copper(ii) complexes with 3-(2-pyridyl)-4,5-dihydro-1H-pyrazoles: synthesis, structural and electrochemical studies
    N. I. Vorozhtsov
    A. G. Majouga
    E. K. Beloglazkina
    A. A. Moiseeva
    G. A. Golubeva
    I. V. Evstaf’ev
    L. A. Sviridova
    N. V. Zyk
    Russian Chemical Bulletin, 2014, 63 : 657 - 661
  • [43] Straightforward and Clean Ultrasound-Promoted Synthesis of 2-(4,5-Dihydro-1H-pyrazol-1-yl) pyrimidines
    Kuhn, Bruna P.
    Malavolta, Juliana L.
    Casagrande, Gleison A.
    Raminelli, Cristiano
    Quina, Frank H.
    Pereira, Claudio M. P.
    Flores, Alex F. C.
    Pizzuti, Lucas
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2015, 26 (06) : 1306 - 1312
  • [44] Copper-catalyzed synthesis of 1,3,4-trisubstituted and 1,3,4,5-tetrasubstituted pyrazoles via [3+2] cycloadditions of hydrazones and nitroolefins
    Shi, Chong
    Ma, Chaowei
    Ma, Haojie
    Zhou, Xiaoqiang
    Cao, Jinhui
    Fan, Yuxing
    Huang, Guosheng
    TETRAHEDRON, 2016, 72 (27-28) : 4055 - 4058
  • [45] Synthesis and antimicrobial screening of novel 2-(5-(4-(allyloxy)3-methoxyphenyl)-1H-pyrazol-3-yl)phenols analogues of 2-(4-(allyloxy)-3-methoxyphenyl)-4H-chromen-4-ones
    Chate, Asha V.
    Nikam, Mukesh D.
    Mahajan, Pravin S.
    Mohekar, Shweta R.
    Gill, Charansingh H.
    ORGANIC COMMUNICATIONS, 2012, 5 (02) : 83 - 98
  • [46] Ultrasound promoted greener synthesis of 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles
    Venzke, Dalila
    Flores, Alex F. C.
    Quina, Frank H.
    Pizzuti, Lucas
    Pereira, Claudio M. P.
    ULTRASONICS SONOCHEMISTRY, 2011, 18 (01) : 370 - 374
  • [47] Molecular Structure of (1-Benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)(4-bromophenyl)methanone: A Combined Experimental and Theoretical Study
    Muhammad, Naeem Ahmed
    Ifzan, Arshad
    Wang Bo
    Shahid, Hameed
    Blal, Ahmad Khan
    Khawaja, Ansar Yasin
    Muhammad, Moazzam Naseer
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 33 (12) : 1749 - 1756
  • [48] Crystal structure of 3-(furan-2-yl)-5-(4-phenylphenyl)-1H-pyrazole - methanol (1:1), C19H14N2O•CH3OH
    Zheng, Chun-Yang
    Sun, Ting-Quan
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2010, 225 (01): : 31 - 33
  • [49] 3-(1H-Pyrrol-2-yl)-1H-pyrazole forms an unusual hydrogen-bonded two-dimensional (3,4)-connected net
    Marriott, Katie E. R.
    Kilner, Colin A.
    Halcrow, Malcolm A.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2009, 65 : O506 - O508
  • [50] Synthesis, anticancer activity and molecular docking study of (E)-4-(3,4Dichlorophenyl)-2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)-3,4- dihydronaphthalen-1(2H)-one derivatives
    Sadanandam, Kudikala
    Pinnoju, Prasad
    Manasa, S. K.
    Sarasija, Madderla
    CHEMICAL BIOLOGY LETTERS, 2024, 11 (01):