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
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
  • [1] Synthesis of 5-(trifluoromethyl)cyclohexane-1,3-dione and 3-amino-5-(trifluoromethyl)cyclohex-2-en-1-one: new trifluoromethyl building block
    Fadeyi, Olugbeminiyi O.
    Okoro, Cosmas O.
    TETRAHEDRON LETTERS, 2008, 49 (32) : 4725 - 4727
  • [2] CHELATE COMPOUNDS OF TRANSITION-METALS WITH TETRAAZA-CHELATE NODE .4. TRICYCLIC CHELATE COMPOUNDS-CU(II) BASED ON HYDRAZONEIMINES OF 1-PHENYLPROPANE-1,2,3-TRIONE, BUTAN-1,2,3-TRIONE, 1-TRIFLUOROMETHYLBUTANE-1,2,3-TRIONE AND 1-TRIFLUOROMETHYL-3-PHENYLPROPANE-1,2,3-TRIONE
    PANOVA, GV
    POTAPOV, VM
    OVCHINNIKOVA, OV
    KOSINA, AN
    ZHURNAL OBSHCHEI KHIMII, 1987, 57 (10): : 2346 - 2353
  • [3] (5S)-5-(Trifluoromethyl)pyrrolidin-2-one as a Promising Building Block for Fluoroorganic Chemistry
    Bezdudny, Andrii V.
    Alekseenko, Anatoliy N.
    Mykhailiuk, Pavel K.
    Manoilenko, Olga V.
    Shishkin, Oleg V.
    Pustovit, Yurii M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1782 - 1785
  • [4] Synthesis of Methylene-Bridged Trifluoromethyl Azoles Using 5-(1,2,3-Triazol-1-yl)enones
    Mittersteiner, Mateus
    Aquino, Estefania C.
    Budragchaa, Tuvshinjargal
    Wessjohann, Ludger A.
    Bonacorso, Helio G.
    Martins, Marcos A. P.
    Zanatta, Nilo
    SYNTHESIS-STUTTGART, 2022, 54 (02): : 439 - 450
  • [5] A One-Pot Domino Synthesis of 5-(Trifluoromethyl)-2-thiazolamine
    Bao, Xue-fei
    Qiao, Xue-jun
    Hou, Xiao
    Fang, Wu-hong
    Liu, Xue-long
    Chen, Guo-liang
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2016, 27 (12) : 2388 - 2391
  • [6] Chemistry of free cyclic vicinal tricarbonyl compounds ('1,2,3-triones'). Part 1. Reaction of diazomethane and its derivatives with 5,5-dimethylcyclohexane-1,2,3-trione (='oxo-dimedone') and related cyclohexane-1,2,3-triones
    Schank, K
    La Vecchia, L
    Lick, C
    HELVETICA CHIMICA ACTA, 2001, 84 (07) : 2071 - 2088
  • [7] 1-Bromo-2-trifluoroacetylcyclobutenes as novel building blocks for the construction of trifluoromethyl substituted heterocycles. Part 1: Synthesis of 5-(trifluoromethyl)-2(5H)-furanones condensed with substituted cyclobutenes
    Koldobskii, Andrey B.
    Tsvetkov, Nikolay P.
    Solodova, Ekaterina V.
    Kalinin, Valery N.
    JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (06) : 714 - 718
  • [8] Crystal Structure of Spiro 5,5-Dimethyl Cyclohexane1,2,3-trione 2-phenylhydrazone and Spectral Characterization of its Transition Metal Complexes
    Seth, Susannah
    Aravindakshan, Kuttamath Kunniyur
    SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2009, 39 (06) : 345 - 350
  • [9] Synthesis and Anti-tuberculosis Activity of 2-[(2-Hydroxy-4-trifluoromethyl-phenylamino)-methylene]-cyclohexane-1,3-dione
    Ahad, Rukhsana
    Lone, Nisar Ahmad
    Bhat, Arshid Iqbal
    Lone, Ali Mohd
    LATIN AMERICAN JOURNAL OF PHARMACY, 2023, 42 (06): : 1196 - 1199
  • [10] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 1,5-DIPHENYL-4-ARYLAZOPYRAZOLES AND 5,5-DIMETHYLCYCLOHEXANE-1,2,3-TRIONE BISHYDRAZONES
    GARG, HG
    SINGHAL, A
    MATHUR, JML
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1973, 62 (03) : 494 - 496