Metal-Free Photoredox Catalyzed Cyclization of O-(2,4-Dinitrophenyl)oximes to Phenanthridines

被引：27
|
作者：
Liu, Xiubin [1 ,2 ]
Qing, Zhixing [1 ,2 ]
Cheng, Pi [1 ,2 ]
Zheng, Xinyu [1 ]
Zeng, Jianguo [1 ,2 ]
Xie, Hongqi [1 ,2 ]
机构：
[1] Hunan Agr Univ, Natl & Prov Union Engn Res Ctr Vet Herbal Med Res, Changsha 410128, Hunan, Peoples R China
[2] Hunan Agr Univ, Hunan Coinnovat Ctr Utilizat Bot Funct Ingredient, Changsha 410128, Hunan, Peoples R China
来源：
MOLECULES | 2016年 / 21卷 / 12期
基金：
中国国家自然科学基金;
关键词：
visible light; photoredox catalysis; eosin Y; O-aryl oximes; phenanthridines; RADICAL TRIFLUOROMETHYLATION; MACLEAYA-CORDATA; ALKALOIDS; IDENTIFICATION; DERIVATIVES; QUINOLINES; GROWTH; FRUITS; NK109;
D O I：
10.3390/molecules21121690
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A metal-free visible-light photoredox-catalyzed intermolecular cyclization reaction of O-2,4-dinitrophenyl oximes to phenanthridines was developed. In this study, the organic dye eosin Y and i-Pr2NEt were used as photocatalyst and terminal reductant, respectively. The oxime substrates were transformed into iminyl radical intermediates by single-electron reduction, which then underwent intermolecular homolytic aromatic substitution (HAS) reactions to give phenanthridine derivatives.
引用
收藏
页数：11
相关论文
共 50 条
  • [1] O-(2,4-Dinitrophenyl) hydroxylamine
    Yang, Zhanhui
    SYNLETT, 2014, 25 (08) : 1186 - 1187
  • [2] Sigmatropic rearrangements of 2,4-dinitrophenyl oximes
    Boyle, PH
    Ali, HDP
    Mc Donald, TJ
    ARKIVOC, 2003, : 67 - 79
  • [3] PRIMARY ALKYL AMINOLYSIS OF O-(2,4-DINITROPHENYL)-P,P'DISUBSTITUTED BENZOPHENONE OXIMES IN BENZENE
    JAIN, AK
    SINGH, P
    ATRAY, N
    SAHOO, BB
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (12): : 1047 - 1052
  • [4] ULTRAVIOLET SPECTRA OF O-(2,4-DINITROPHENYL)OXIMES AND 2,4-DINITROPHENYLHYDRAZONES - TRANSMISSION OF ELECTRONIC EFFECTS THROUGH O AND NH GROUPS
    RAPPOPORT, Z
    SHERADSKY, T
    JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1967, (09): : 898 - +
  • [5] MICELLAR EFFECT ON METHYLAMINOLYSIS OF O-(2,4-DINITROPHENYL)CYCLOHEXANONE OXIME
    JAIN, AK
    BHATTACHARJEE, G
    VELU, VK
    KUMAR, A
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 1989, 28 (11): : 992 - 993
  • [6] 0-(2,4-DINITROPHENYL) OXIMES . SYNTHESIS AND CYCLIZATION TO 5,7-DINITROBENZOFURANS
    SHERADSKY, T
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1967, 4 (03) : 413 - +
  • [7] EFFICIENT AZIRIDINATION OF α,β-UNSATURATED KETONES WITH O-(2,4-DINITROPHENYL)-HYDROXYLAMINE
    Wang, Jin-jia
    Lao, Jin-hua
    Li, Xue-ming
    Lu, Rui-jiong
    Miao, Hui
    Yan, Ming
    SYNTHETIC COMMUNICATIONS, 2012, 42 (11) : 1577 - 1584
  • [8] Aminolysis of O-(2,4-dinitrophenyl)-p,p'-disubstituted benzophenone oximes in benzene: Evidence for Hirst's mechanism
    Jain, AK
    Singh, P
    Sahoo, BB
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1996, 9 (11) : 770 - 776
  • [9] KINETIC-STUDIES ON THE AMINOLYSIS OF O-(2,4-DINITROPHENYL)-CYCLOPENTANONE OXIME IN BENZENE
    JAIN, AK
    GUPTA, VK
    SINGH, P
    KUMAR, A
    REACTION KINETICS AND CATALYSIS LETTERS, 1991, 43 (01): : 117 - 125
  • [10] Aminolysis of O-(2,4-Dinitrophenyl)-p,p-disubstituted Benzophenone Oximes in Benzene: Evidence for Jack Hirst's Mechanism
    Jain, A. K.
    Singh, P.
    Sahoo, B. B.
    Journal of Physical Organic Chemistry, 1996, 9 (11)
12345