One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers

被引:7
|
作者
Liu, Cuibo [1 ]
Yin, Xuguang [1 ]
Chang, Jing [1 ]
Tang, Xiangyang [1 ]
Zhang, Bin [1 ,2 ]
机构
[1] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China
关键词
Polyfluoroarenes; C-F bond cleavage; One-pot two-step; o-Arylated oximes; PENTAFLUOROBENZONITRILE; POLYFLUOROARENES; FLUORINE; REAGENTS; ACID;
D O I
10.1016/j.jfluchem.2014.06.011
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldehydes or ketones oximes followed by the SNAr reaction with pentafluorobenzonitrile via the high selective C-F bond cleavage. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:101 / 108
页数:8
相关论文
共 50 条
  • [1] Transformation of Alkynes into α- or β-Difluorinated Alkyl Azides by an Efficient One-Pot Two-Step Procedure
    Li, Huaizhi
    Reddy, Bhoomireddy Rajendra Prasad
    Bi, Xihe
    ORGANIC LETTERS, 2019, 21 (23) : 9358 - 9362
  • [2] One-pot two-step facile synthesis of 2,3,5,6-tetralluorobenzonitrile-containing dithiocarbamic acid esters
    Yin, Xuguang
    Guo, Yamei
    Liu, Cuibo
    Wang, Zhifang
    Zhang, Bin
    TETRAHEDRON LETTERS, 2015, 56 (36) : 5135 - 5139
  • [3] One-Pot Two-Step Synthesis of Isochromene-Fused CF3-Substituted Pyrazoles
    Nikolic, Andrea M.
    Zivkovic, Filip
    Selakovic, Zivota
    Wipf, Peter
    Opsenica, Igor M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (34) : 5616 - 5619
  • [4] L-Proline-Functionalized Fe3O4 Nanoparticles as an Efficient Nanomagnetic Organocatalyst for Highly Stereoselective One-Pot Two-Step Tandem Synthesis of Substituted Cyclopropanes
    Firouzi-Haji, Razieh
    Maleki, Ali
    CHEMISTRYSELECT, 2019, 4 (03): : 853 - 857
  • [5] Efficient and Convenient Synthesis of N3-(Acyloxymethyl)dihydropyrimidinones by a One-Pot Two-Step Method
    Quan, Zheng-Jun
    Ren, Rong-Guo
    Da, Yu-Xia
    Zhang, Zhang
    Wang, Xi-Cun
    LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (03) : 188 - 192
  • [6] An efficient one-pot, two-step synthesis of 4-substituted 1-heteroarylpiperazines under microwave irradiation conditions
    Wang, Hong-Jun
    Earley, William G.
    Lewis, Robert M.
    Srivastava, Rajiv R.
    Zych, Andrew J.
    Jenkins, David M.
    Fairfax, David J.
    TETRAHEDRON LETTERS, 2007, 48 (17) : 3043 - 3046
  • [7] One-pot, two-step synthesis of substituted triazoloquinoxalinone starting from 3-hydrazineylquinoxalin-2(1H)-one
    Patil, Vikas S.
    Yadavalli, Subba Rao
    Merugu, Ramchander
    Swamy, S. J.
    Devunuri, Nagaraju
    SYNTHETIC COMMUNICATIONS, 2021, 51 (13) : 1994 - 2000
  • [8] Efficient synthesis of arylaldehyde oxime ethers functionalised with 3,4-dihydropyrimidinones and 2,5-quinazolinediones via a one-pot two-step method
    Quan, Zheng-Jun
    Tang, Xue-Hong
    Da, Yu-Xia
    Zhang, Zhang
    Wang, Xi-Cun
    JOURNAL OF CHEMICAL RESEARCH, 2013, (01) : 30 - 33
  • [9] One-pot two-step facile synthesis of 2,3,4,5-tetra substituted dihydrooxazoles and their antimicrobial activity
    Tiwari, Shailendra
    Pathak, Poonam
    Singh, Kamal Pratap
    Sagar, Ram
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (16) : 3802 - 3805
  • [10] A two-step, one-pot route to swap the pyrroline moiety in meso-tetraaryldihydroxy-chlorins with an O/N-substituted oxazoline
    Ogikubo, Junichi
    Worlinsky, Jill L.
    Fu, You-Jun
    Brueckner, Christian
    TETRAHEDRON LETTERS, 2013, 54 (13) : 1707 - 1710