Acid catalyzed rearrangements of aryl 3-(2-nitroaryl)oxiran-2-yl ketones

被引：5
|
作者：
Mamedov, V. A. [1 ]
Mamedova, V. L. [1 ]
Gubaidullin, A. T. [1 ]
Krivolapov, D. B. [1 ]
Khikmatova, G. Z. [1 ]
Mahrous, E. M. [1 ]
Korshin, D. E. [1 ]
Sinyashin, O. G. [1 ]
机构：
[1] Russian Acad Sci, Kazan Sci Ctr, Fed Res Ctr, AE Arbuzov Inst Organ & Phys Chem, 8 Ul Arbuzova, Kazan 420088, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2020年 / 69卷 / 03期
基金：
俄罗斯科学基金会;
关键词：
oxiranes; aryl 3-(2-nitroaryl)oxiran-3-yl ketones; rearrangements; anthranilic acid derivatives; 2-(2-oxo-2-arylacetamido)benzoic acids; 3-hydroxyquinolin-4-ones; RING-OPENING REACTIONS; EPOXIDES; PARTICIPATION; CYCLIZATION; TRENDS;
D O I：
10.1007/s11172-020-2791-x
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Studies of chemical behavior of aryl 3-(2-nitrophenyl)oxiran-3-yl ketones in acidic medium revealed the possible occurrence of two competitive rearrangements leading to 2-(2-oxo-2-arylacetamido)benzoic acids and 3-hydroxyquinolin-4(1H)-ones.
引用
收藏
页码：510 / 516
页数：7
相关论文
共 50 条
  • [21] Synthesis of key intermediate for (+)-tofacitinib through CoIII(salen)-catalyzed two stereocentered hydrolytic kinetic resolution of (±)-methyl-3-(oxiran-2-yl)butanoate
    Kamble, Rohit B.
    Suryavanshi, Gurunath
    SYNTHETIC COMMUNICATIONS, 2018, 48 (09) : 1045 - 1051
  • [22] A Long-Wavelength, Fluorogenic Probe for Epoxide Hydrolase: 7-(2-(Oxiran-2-yl)ethoxy) Resorufin
    Shen, Wei
    Zhang, Jiaming
    Mao, Genjun
    Jiang, Keyi
    Zhu, Qing
    BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2009, 32 (09) : 1496 - 1499
  • [23] Acid-catalyzed reactions of (3-(naphthalen-2-yl)-2,2-bis(trimethylsilyl)oxiran. A new synthesis of functional-group-substituted vinylsilanes
    Safa, Kazem D.
    Behmagham, Farnaz
    Ghorbanpour, Khatereh
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (09) : 1840 - 1844
  • [24] SYNTHESIS OF ARYL 3-(2-IMIDAZOLYL)PROPYL KETONES
    DAVIS, FS
    HUANG, LF
    BAUER, L
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) : 915 - 920
  • [25] 5-tert-butylperoxy-5-(oxiran-2-yl)-1-(prop-2-ynyl)-pyrrolidin-2-one
    Coles, SJ
    Hibbs, DE
    Hursthouse, MB
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2001, 57 : O66 - O67
  • [26] Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone
    Peru, Aurelien A. M.
    Flourat, Amandine L.
    Gunawan, Christian
    Raverty, Warwick
    Jevric, Martyn
    Greatrex, Ben W.
    Allais, Florent
    MOLECULES, 2016, 21 (08)
  • [27] Palladium-catalyzed aminocarbonylative cyclization of benzyl chlorides with 2-nitroaryl alkynes to construct indole derivatives
    Wang, Qi
    Yao, Lingyun
    Wang, Jian-Shu
    Ying, Jun
    Wu, Xiao-Feng
    Molecular Catalysis, 2022, 524
  • [28] A new method for the synthesis of 2-aryl-1H-benzimidazoles:: Selenium-catalyzed reductive N-heterocyclization of benzylidene(2-nitroaryl)amines with carbon monoxide
    Nishiyama, Y
    Fujimoto, M
    Sonoda, N
    SYNLETT, 2006, (01) : 109 - 111
  • [29] Divergent Synthesis of 3-(Indol-2-yl)quinoxalin-2-ones and 4-(Benzimidazol-2-yl)-3-methyl(aryl)cinnolines via Polyphosphoric Acid (PPA)-Mediated Intramolecular Rearrangements of 3-(Methyl/aryl(2-phenylhydrazono)methyl)quinoxalin-2-ones
    Mamedov, Vakhid A.
    Mustakimova, Liliya V.
    Qu, Zheng-Wang
    Zhu, Hui
    Syakaev, Victor V.
    Galimullina, Venera R.
    Shamsutdinova, Leisan R.
    Rizvanov, Il'dar Kh.
    Gubaidullin, Aidar T.
    Sinyashin, Oleg G.
    Grimme, Stefan
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 16864 - 16890
  • [30] Palladium-catalyzed aminocarbonylative cyclization of benzyl chlorides with 2-nitroaryl alkynes to construct indole derivatives
    Wang, Qi
    Yao, Lingyun
    Wang, Jian-Shu
    Ying, Jun
    Wu, Xiao-Feng
    MOLECULAR CATALYSIS, 2022, 524
12345