Synthesis of N-Nitroso CHF2-Pyrazolines and Their Transformation into CHF2-Isoxazolines and -Pyrazoles

被引:25
作者
Lebed, Pavlo S. [1 ,2 ,3 ]
Fenneteau, Johan [4 ]
Wu, Yong [5 ,6 ]
Cossy, Janine [4 ]
Mykhailiuk, Pavel K. [1 ]
机构
[1] Taras Shevchenko Natl Univ Kyiv, Dept Chem, Volodymyrska 64, UA-01601 Kiev, Ukraine
[2] Enamine Ltd, Chervonotkatska 78, UA-02094 Kiev, Ukraine
[3] Taras Shevchenko Natl Univ Kyiv, ChemBioCtr, Volodymyrska 64, UA-01601 Kiev, Ukraine
[4] PSL Res Univ, ESPCI Paris 8281, Lab Chim Organ, Inst Chem Biol & Innovat CBI UMR, 10 Rue Vauquelin, F-75231 Paris 05, France
[5] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting, Chengdu 610041, Sichuan, Peoples R China
[6] Sichuan Univ, West China Sch Pharm, Dept Med Chem, Chengdu 610041, Sichuan, Peoples R China
关键词
Fluorine; Heterocycles; Alkenes; Diazo compounds; Cycloaddition; Fluorinated compounds; FLUORINATED TEBUFENPYRAD ANALOGS; ELECTRON-DEFICIENT ALKYNES; IN-SITU GENERATION; ONE-POT SYNTHESIS; TRIFLUOROMETHYL DIAZOMETHANE; MEDICINAL CHEMISTRY; 3-COMPONENT SYNTHESIS; 2,2,2-TRIFLUORODIAZOETHANE; CYCLOADDITION; DIFLUOROMETHYLATION;
D O I
10.1002/ejoc.201700803
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Nitroso CHF2-pyrazolines were synthesized from in situ generated difluoromethyldiazomethane (CF2HCHN2), tert-butyl isonitrite (tBuONO), and alkenes. The synthesis of representative CHF2-pyrazoles and CHF2-oxazolines was also performed.
引用
收藏
页码:6114 / 6120
页数:7
相关论文
共 71 条
  • [11] Duan S.-W., 2016, E EROS ENCY REAGENTS
  • [12] Synthesis of Functionalized 4-Fluoropyridazines
    Feraldi-Xypolia, Alexandra
    Fredj, Gregory
    Tran, Gael
    Tsuchiya, Tomoki
    Vors, Jean-Pierre
    Mykhailiuk, Pavel
    Pardo, Domingo Gomez
    Cossy, Janine
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 927 - 935
  • [13] Synthesis of New Fluorinated Tebufenpyrad Analogs with Acaricidal Activity Through Regioselective Pyrazole Formation
    Fustero, Santos
    Roman, Raquel
    Sanz-Cervera, Juan F.
    Simon-Fuentes, Antonio
    Bueno, Jorge
    Villanova, Salvador
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) : 8545 - 8552
  • [14] Improved regioselectivity in pyrazole formation through the use of fluorinated alcohols as solvents:: Synthesis and biological activity of fluorinated Tebufenpyrad analogs
    Fustero, Santos
    Roman, Raquel
    Sanz-Cervera, Juan F.
    Simon-Fuentes, Antonio
    Cunat, Ana C.
    Villanova, Salvador
    Murguia, Marcelo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) : 3523 - 3529
  • [15] From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles
    Fustero, Santos
    Sanchez-Rosello, Maria
    Barrio, Pablo
    Simon-Fuentes, Antonio
    [J]. CHEMICAL REVIEWS, 2011, 111 (11) : 6984 - 7034
  • [16] "Reported, but Still Unknown." A Closer Look into 3,4-Bis- and 3,4,5-Tris(trifluoromethyl)pyrazoles
    Gerus, Igor I.
    Mironetz, Roman X.
    Kondratov, Ivan S.
    Bezdudny, Andrei V.
    Dmytriv, Yurii V.
    Shishkin, Oleg V.
    Starova, Viktoriia S.
    Zaporozhets, Olga A.
    Tolmachev, Andrey A.
    Mykhailiuk, Pavel K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) : 47 - 56
  • [17] 2,2,2-Trifluoroethylamine and 2,2,2-trifluorodiazoethane
    Gilman, H
    Jones, RG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 : 1458 - 1460
  • [18] Synthesis of diversely fluorinated pyrazoles as novel active agrochemical ingredients
    Giornal, Florence
    Pazenok, Sergiy
    Rodefeld, Lars
    Lui, Norbert
    Vors, Jean-Pierre
    Leroux, Frederic R.
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 : 2 - 11
  • [19] Gouverneur V., 2012, Fluorine in Pharmaceutical and Medicinal Chemistry: from biophysical aspects to clinical applications
  • [20] The many roles for fluorine in medicinal chemistry
    Hagmann, William K.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) : 4359 - 4369