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
[31]   Silver(I)-Catalyzed N-Trifluoroethylation of Anilines and O-Trifluoroethylation of Amides with 2,2,2-Trifluorodiazoethane [J].
Luo, Haiqing ;
Wu, Guojiao ;
Zhang, Yan ;
Wang, Jianbo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) :14503-14507
[32]   Fluorinated diazoalkanes - a versatile class of reagents for the synthesis of fluorinated compounds [J].
Mertens, Lucas ;
Koenigs, Rene M. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (45) :10547-10556
[33]   Fluoroalkyl-Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines [J].
Mertens, Lucas ;
Hock, Katharina J. ;
Koenigs, Rene M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (28) :9542-9545
[34]  
Molander G.A., 2014, ANGEW CHEM INT EDIT, V126, P14405
[35]   Diastereoselective Synthesis of Vicinally Bis(trifluoromethylated) Alkylboron Compounds through Successive Insertions of 2,2,2-Trifluorodiazoethane [J].
Molander, Gary A. ;
Ryu, DaWeon .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (51) :14181-14185
[36]  
Morandi B., 2010, Angew. Chem, V122, P950, DOI [10.1002/ange.200905573, DOI 10.1002/ANGE.200905573]
[37]   Iron-Catalyzed Cyclopropanation with Trifluoroethylamine Hydrochloride and Olefins in Aqueous Media: In Situ Generation of Trifluoromethyl Diazomethane [J].
Morandi, Bill ;
Carreira, Erick M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (05) :938-941
[38]   Fluorine in pharmaceuticals:: Looking beyond intuition [J].
Mueller, Klaus ;
Faeh, Christoph ;
Diederich, Francois .
SCIENCE, 2007, 317 (5846) :1881-1886
[39]  
Mykdailiuk P.k, 2015, ANGEW CHEM, V127, P6658
[40]  
Mykhailiuk P. K., CHEM EUR J