Synthesis of 5-(trifluoromethyl)cyclohexane-1,2,3-trione (cVTC): new trifluoromethyl building block

被引：3
|
作者：
Obi, Chibuike D. [1 ]
Okoro, Cosmas O. [1 ]
机构：
[1] Tennessee State Univ, Dept Chem, 3500 John A Merritt Blvd, Nashville, TN 37209 USA
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 47期
关键词：
Trifluoromethyl; Vicinal tricarbonyl; Cycloalkanone; Fluorinated Cyclohexane-1,2-3-trione; Triketone; VICINAL TRICARBONYLS; 1,3-DICARBONYL COMPOUNDS; CHEMISTRY;
D O I：
10.1016/j.tetlet.2016.10.043
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple synthesis of 5-(trifluoromethyl)cyclohexane-1,2,3-trione is demonstrated in one step, by reacting 5-(trifluoromethyl)cyclohexane-1,3-dione with cerium(IV)ammonium nitrate (CAN) in methanol. The compound represents a highly functionalized oxygen-rich reactive intermediate for the synthesis of organic and heterocyclic compounds containing fluorine. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5259 / 5261
页数：3
相关论文
共 50 条
  • [21] SYNTHESIS OF 2-(ALPHA,ALPHAH, OMEGAH-POLYFUOROALKOXY)-5-(TRIFLUOROMETHYL)-META-PHENYLENE DIISOCYANATES
    MALICHEN.BF
    YAZLOVIT.AV
    JOURNAL OF GENERAL CHEMISTRY USSR, 1969, 39 (10): : 2261 - &
  • [22] Syntheses and insecticidal activity of new 2-(5-(trifluoromethyl)pyridyloxymethyl)-1,3,4-oxadiazoles
    Cao, S
    Qian, XH
    Song, GH
    Huang, QC
    JOURNAL OF FLUORINE CHEMISTRY, 2002, 117 (01) : 63 - 66
  • [23] Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam
    Huang, Shuai Shuai
    Zheng, Zhan Jiang
    Cui, Yu Ming
    Xu, Zheng
    Yang, Ke Fang
    Xu, Li Wen
    SYNTHESIS-STUTTGART, 2019, 51 (22): : 4249 - 4252
  • [24] DAST promotes the synthesis of new 5-(trifluoromethyl)-3-(1,1-difluoroethan-2-yl)-1H-pyrazoles
    Bonacorso, Helio G.
    Porte, Liliane M. F.
    Cechinel, Cleber A.
    Paim, Gisele R.
    Deon, Everton D.
    Zanatta, Nilo
    Martins, Marcos A. P.
    TETRAHEDRON LETTERS, 2009, 50 (13) : 1392 - 1394
  • [25] Silver-Mediated [3+2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles
    Yang, Hefei
    Lu, Shu-Ning
    Chen, Zhengkai
    Wu, Xiao-Feng
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05): : 4361 - 4370
  • [26] A One-Pot Domino Synthesis of 5-(Trifluoromethyl)-2-thiazolamine (vol 27, pg 2388, 2016)
    Bao, Xue-fei
    Qiao, Xue-jun
    Hou, Xiao
    Liu, Wu-long
    Chen, Guo-liang
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2023, 34 (06) : 894 - 895
  • [27] Synthesis of 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines from 3-nitro-2-(trifluoromethyl)-2H-chromenes and aminoenones derived from acetylacetone and cyclic amines
    Korotaev, Vladislav Yu.
    Barkov, Alexey Yu.
    Sosnovskikh, Vyacheslav Ya.
    TETRAHEDRON LETTERS, 2013, 54 (24) : 3091 - 3093
  • [28] Synthesis of 5-(Trifluoromethyl)-2,5-dihydro-1,2λ5-oxaphospholes by a One-Pot Three-Component Reaction
    Fan, Hua-Fang
    Wang, Xiao-Wei
    Zhao, Jing-Wei
    Li, Xin-Jin
    Gao, Jin-Ming
    Zhu, Shi-Zheng
    SYNTHESIS-STUTTGART, 2012, 44 (21): : 3315 - 3320
  • [29] Design, synthesis, and biological evaluation of a library of 1-(2-thiazolyl)-5-(trifluoromethyl)pyrazole-4-carboxamides
    Donohue, BA
    Michelotti, EL
    Reader, JC
    Reader, V
    Stirling, M
    Tice, CM
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (01): : 23 - 32
  • [30] SYNTHESIS AND EVALUATION OF PHARMACOLOGICAL AND PHARMACOKINETIC PROPERTIES OF MONOPROPYL ANALOGS OF 5-[[(TRIFLUOROMETHYL)SULFONYL]OXY]-2-AMINOTETRALIN, 7-[[(TRIFLUOROMETHYL)SULFONYL]OXY]-2-AMINOTETRALIN, AND 8-[[(TRIFLUOROMETHYL)SULFONYL]OXY]-2-AMINOTETRALIN - CENTRAL DOPAMINE AND SEROTONIN RECEPTOR ACTIVITY
    SONESSON, C
    BARF, T
    NILSSON, J
    DIJKSTRA, D
    CARLSSON, A
    SVENSSON, K
    SMITH, MW
    MARTIN, IJ
    DUNCAN, JN
    KING, LJ
    WIKSTROM, H
    JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (08) : 1319 - 1329
12345