A Concise and Efficient Approach to 2,6-Disubstituted 4-Fluoropyrimidines from α-CF3 Aryl Ketones

被引:14
|
作者
Liu, Fangran [1 ,2 ]
Zhang, Xiaofei [2 ]
Qian, Qun [1 ]
Yang, Chunhao [2 ]
机构
[1] Shanghai Univ, Dept Chem, 99 Shang Da Rd, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China
来源
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 02期
基金
中国国家自然科学基金;
关键词
fluoropyrimidine; alpha-CF3 aryl ketone; metal-free; mild conditions; PYRIMIDINE; INHIBITORS; FLUORINE; DESIGN; CHEMISTRY; DISCOVERY;
D O I
10.1055/s-0039-1690248
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, a concise and efficient protocol to synthesize a series of 2,6-disubstituted 4-fluoropyrimidines as universal and useful building blocks in medicinal chemistry is reported. From readily accessible alpha-CF3 aryl ketones and different amidine hydrochlorides, this method provides a very practical approach to this kind of compounds under mild conditions with good to excellent yields.
引用
收藏
页码:273 / 280
页数:8
相关论文
共 26 条
  • [1] Palladium-catalyzed direct approach to α-CF3 aryl ketones from arylboronic acids
    Jiang, Bo
    Zhang, Xiaofei
    Yang, Chunhao
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (10): : 1724 - 1727
  • [2] Synthesis of 4,6-Disubstituted 2-Thioxo-1,2-dihydropyridine-3-carbonitriles by the Reaction of Acetylenic Ketones with Cyanothioacetamide
    Buryi, D. S.
    Dotsenko, V. V.
    Levashov, A. S.
    Lukina, D. Yu.
    Strelkov, V. D.
    Aksenov, N. A.
    Aksenova, I. V.
    Netreba, E. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (05) : 886 - 895
  • [3] Diversity-Oriented Approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-Substituted Arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes
    Emer, Enrico
    Twilton, Jack
    Tredwell, Matthew
    Calderwood, Samuel
    Collier, Thomas Lee
    Liegault, Benoit
    Taillefer, Marc
    Gouvemeur, Veronique
    ORGANIC LETTERS, 2014, 16 (22) : 6004 - 6007
  • [4] nBu4N+[AgI(CF3)2]-: Trifluoromethylated Argentate Derived from Fluoroform and Its Reaction with (Hetero)Aryl Diazonium Salts
    Lu, Zehai
    Wang, Linhua
    Hughes, Matthew
    Smith, Stephen
    Shen, Qilong
    ORGANIC LETTERS, 2023, 26 (14) : 2773 - 2777
  • [5] Consecutive Three-Component Synthesis of 2,6-Disubstituted Pyrimid-4(3H)-ones and 1,5-Disubstituted 3-Hydroxypyrazoles Initiated by Copper(I)-Catalyzed Carboxylation of Terminal Alkynes
    Schreiner, Ella
    Braun, Stephan
    Kwasnitschka, Christiane
    Frank, Walter
    Mueller, Thomas J. J.
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 3135 - 3147
  • [6] Reactions of 2-Mono- and 2,6-Disubstituted 4-Pyrones with Phenylhydrazine as General Method for the Synthesis of 3-(N-Phenylpyrazolyl)Indoles
    Obydennov, D. L.
    Usachev, B. I.
    Sosnovskikh, V. Ya.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 50 (10) : 1388 - 1403
  • [7] A CONCISE ROUTE FOR THE ONE-POT MULTI-COMPONENT SYNTHESIS OF 4,6-DISUBSTITUTED 2-AMINOPYRIDINE-3-CARBONITRILES AND PYRANOPYRAZOLES USING COBALT (II) NITRATE HEXAHYDRATE AS CATALYST
    Pejman, Hamed
    Hazeri, Nourallah
    Fatahpour, Maryam
    Faroughi Niya, Homayoun
    REVUE ROUMAINE DE CHIMIE, 2019, 64 (03) : 241 - 247
  • [8] Copper-Catalyzed Synthesis of 4-CF3-1,2,3-Triazoles: An Efficient and Facile Approach via Click Reaction
    Tang, Tinghong
    Chen, Cuiting
    Fu, Xin
    Xu, Huilan
    Wu, Luyong
    Chen, Wenhao
    MOLECULES, 2024, 29 (06):
  • [9] Antibacterial 3,6-Disubstituted 4-Hydroxy-5,6-dihydro-2H-pyran-2-ones from Serratia plymuthica MF371-2
    Bjerketorp, Joakim
    Levenfors, Jolanta J.
    Sahlberg, Christer
    Nord, Christina L.
    Andersson, Pierre F.
    Guss, Bengt
    Oberg, Bo
    Broberg, Anders
    JOURNAL OF NATURAL PRODUCTS, 2017, 80 (11): : 2997 - 3002
  • [10] Identification of 2,6-Disubstituted 3H-Imidazo[4,5-b]pyridines as Therapeutic Agents for Dysferlinopathies through Phenotypic Screening on Patient-Derived Induced Pluripotent Stem Cells
    Takada, Hiroyuki
    Kaieda, Akira
    Tawada, Michiko
    Nagino, Tomoko
    Sasa, Katsunori
    Oikawa, Tatsuo
    Oki, Akiko
    Sameshima, Tomoya
    Miyamoto, Kazumasa
    Miyamoto, Makoto
    Kokubu, Yuko
    Tozawa, Ryuichi
    Sakurai, Hidetoshi
    Saito, Bunnai
    JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (20) : 9175 - 9187