A simple, modular method for the synthesis of 3,4,5-trisubstituted pyrazoles

被引:66
|
作者
McLaughlin, Mark [1 ]
Marcantonio, Karen [1 ]
Chen, Cheng-yi [1 ]
Davies, Ian W. [1 ]
机构
[1] Merck Res Labs, Proc Res, Rahway, NJ 07065 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 11期
关键词
D O I
10.1021/jo800321p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modular approach for the regiocontrolled preparation of pyrazoles bearing substituents on all three carbon atoms is described. Central to this method is the use of a switchable metal-directing group (MDG) to enable sequential direct lithiation of the 3- and 5-positions of the pyrazole ring. Pyrazole boronic esters obtained from these lithiated intermediates can undergo efficient Suzuki cross-coupling under the developed nonaqueous conditions, which minimize undesirable protolytic deboronation. Halogenation of the 4-position provides the means for substitution at the remaining carbon atom.
引用
收藏
页码:4309 / 4312
页数:4
相关论文
共 50 条
  • [1] Synthesis of 3,4,5-trisubstituted isoxazolines
    Leighton, Taren
    Henson, Kyle
    Mosher, Michael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [2] Synthesis and characterization of 3,4,5-trisubstituted isoxazoline
    Tekade, PV
    Patil, K
    Bodkhe, PS
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (02) : 1340 - 1342
  • [3] Catalytic Enantioselective Synthesis of 3,4,5-Trisubstituted Isoxazoline N-Oxides and Regioselective Synthesis of 3,4,5-Trisubstituted Isoxazoles
    Sahoo, Subas Chandra
    Pan, Subhas Chandra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (06) : 1385 - 1389
  • [4] One-Pot, Three-Component Approach to the Synthesis of 3,4,5-Trisubstituted Pyrazoles
    Kamal, Ahmed
    Sastry, K. N. Visweswara
    Chandrasekhar, D.
    Mani, Geeta Sai
    Adiyala, Praveen Reddy
    Nanubolu, Jagadeesh Babu
    Singarapu, Kiran Kumar
    Maurya, Ram Awatar
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4325 - 4335
  • [5] Synthesis of 3,4,5-Trisubstituted 1H-Pyrazoles Based on Diazoketones with a Diterpene Fragment
    Gindullina, G. M.
    Nugumanov, T. R.
    Sakhautdinov, I. M.
    CHEMISTRY OF NATURAL COMPOUNDS, 2024, 60 (06) : 1114 - 1118
  • [6] NITRIC ACID EXTRACTION BY 3,4,5-TRISUBSTITUTED PYRAZOLES AND 1,3,4,5-TETRASUBSTITUTED PYRAZOLES
    DZIOMKO, VM
    AVILINA, VN
    KRASOVA, LN
    IVANOV, OV
    ZHURNAL NEORGANICHESKOI KHIMII, 1971, 16 (06): : 1672 - &
  • [7] Synthesis and Antiprotozoal Profile of 3,4,5-Trisubstituted Isoxazoles
    不详
    CHEMISTRYOPEN, 2021, 10 (10) : 930 - 930
  • [8] Synthesis and characterization of 3,4,5-trisubstituted isoxazolines and isoxazoles
    Bodkhe, PS
    Patil, KN
    Doshi, AG
    ASIAN JOURNAL OF CHEMISTRY, 2003, 15 (03) : 1715 - 1718
  • [9] EXTRACTION OF METAL IONS BY 1,3,4,5-TETRA- AND 3,4,5-TRISUBSTITUTED PYRAZOLES
    DZIOMKO, VM
    AVILINA, VN
    IVANOV, OV
    DOKLADY AKADEMII NAUK SSSR, 1969, 184 (01): : 98 - &
  • [10] Design, synthesis and antitumor activity of 3,4,5-Trisubstituted Isoxazoles
    Duan, Kanghui
    Tan, Fuxing
    Xie, Hongming
    Liu, Haiwang
    Zhang, Yingjun
    Jiang, Huanfeng
    Wu, Wanqing
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY REPORTS, 2024, 12