Selective Incorporation of Fluorine in Pyrazoles

被引:63
作者
Sloop, Joseph C. [1 ]
Holder, Cory [2 ]
Henary, Maged [2 ]
机构
[1] Georgia Gwinnett Coll, Sch Sci & Technol, Lawrenceville, GA 30043 USA
[2] Georgia State Univ, Dept Chem, Atlanta, GA 30302 USA
关键词
Synthetic methods; Fluorination; Fluorine; Nitrogen heterocycles; ONE-POT SYNTHESIS; CATALYZED N-ARYLATION; REGIOSELECTIVE SYNTHESIS; 3-COMPONENT SYNTHESIS; TEBUFENPYRAD ANALOGS; AZOMETHINE IMINES; DERIVATIVES; EFFICIENT; CYCLOADDITION; CYCLIZATION;
D O I
10.1002/ejoc.201500258
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrazoles are highly essential heterocyclic structures prevalent in biologically active products used widely throughout various disciplines of chemical industry-including medicine and agriculture. The efficacy of these pyrazole species is enhanced through the introduction of fluorine and corresponding functionalities; therefore, synthetic methods for the fluorination of these structures is highly appealing which follows the overall trend of increasing interest in fluorination chemistry. Toward assimilating the known techniques for fluorine incorporation to the pyrazole heterocyclic structure we have reviewed both the new and traditional synthetic approaches to the assembly of functionalized pyrazole derivatives. Specifically, efficient synthetic methods and regioselective incorporation of fluorine and fluorine containing functional groups into different pyrazole ring systems are examined.
引用
收藏
页码:3405 / 3422
页数:18
相关论文
共 50 条
  • [31] AIEE phenomenon: tetraaryl vs. triaryl pyrazoles
    Mukherjee, Sayani
    Salini, P. S.
    Srinivasan, A.
    Peruncheralathan, S.
    CHEMICAL COMMUNICATIONS, 2015, 51 (96) : 17148 - 17151
  • [32] The use of elemental fluorine for selective direct fluorinations
    Moilliet, JS
    JOURNAL OF FLUORINE CHEMISTRY, 2001, 109 (01) : 13 - 17
  • [33] Highly selective removal of fluorine from wastewater containing phosphorus and fluorine in a microreaction system
    Chen, Qingchuan
    Deng, Jian
    Luo, Guangsheng
    SEPARATION AND PURIFICATION TECHNOLOGY, 2025, 358
  • [34] Identification of Genes Essential for Sulfamate and Fluorine Incorporation During Nucleocidin Biosynthesis
    Pasternak, A. R. Ola
    Bechthold, Andreas
    Zechel, David L.
    CHEMBIOCHEM, 2022, 23 (15)
  • [35] Phase-Transfer-Catalyzed Asymmetric Synthesis of Chiral N-Substituted Pyrazoles by Aza-Michael Reaction
    Lee, Su-Jeong
    Bae, Ju-Yeon
    Cho, Chang-Woo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) : 6495 - 6502
  • [36] THE INCORPORATION OF FLUORINE IN TOURMALINE: INTERNAL CRYSTALLOGRAPHIC CONTROLS OR EXTERNAL ENVIRONMENTAL INFLUENCES?
    Henry, Darrell J.
    Dutrow, Barbara L.
    CANADIAN MINERALOGIST, 2011, 49 (01) : 41 - 56
  • [37] Synthesis of Pyrazoles via Electrophilic Cyclization of Alkynes Containing Thiophene
    Cetin, Adnan
    LETTERS IN ORGANIC CHEMISTRY, 2016, 13 (04) : 310 - 315
  • [38] Transition Metal-free C-H Sulfonylation and Pyrazole Annulation Cascade for the Synthesis of 4-Sulfonyl Pyrazoles
    Tian, Lihong
    Wan, Jie-Ping
    Sheng, Shouri
    CHEMCATCHEM, 2020, 12 (09) : 2533 - 2537
  • [39] Base-mediated formal [3+2] cycloaddition of β,γ-alkenyl esters and p-TsN3 for the synthesis of pyrazoles
    Zhao, Mi-Na
    Zhang, Mei-Na
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    SCIENCE BULLETIN, 2017, 62 (07) : 493 - 496
  • [40] Selective synthesis of poly-substituted fluorine-containing pyridines and dihydropyrimidines via cascade C-F bond cleavage protocol
    Chen, Zixian
    Zhu, Jiangtao
    Xie, Haibo
    Li, Shan
    Wu, Yongming
    Gong, Yuefa
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (16) : 5682 - 5691