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
  • [41] Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines
    Tang, Conghui
    Yuan, Yizhi
    Jiao, Ning
    ORGANIC LETTERS, 2015, 17 (09) : 2206 - 2209
  • [42] Transition Metal-Free Oxidative Radical Decarboxylation/Cyclization for the Construction of 6-Alkyl/Aryl Phenanthridines
    Lu, Shichao
    Gong, Yaling
    Zhou, Demin
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18): : 9336 - 9341
  • [43] CONCERTED MECHANISM OF THE AMINOLYSIS OF O-ETHYL S-(2,4-DINITROPHENYL) THIOCARBONATE
    CASTRO, EA
    IBANEZ, F
    SALAS, M
    SANTOS, JG
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16): : 4819 - 4821
  • [44] ELECTROPHILIC AMINATION OF A SINGLE METHIONINE RESIDUE LOCATED AT THE ACTIVE-SITE OF D-AMINO-ACID OXIDASE BY O-(2,4-DINITROPHENYL)HYDROXYLAMINE
    DSILVA, C
    WILLIAMS, CH
    MASSEY, V
    BIOCHEMISTRY, 1986, 25 (19) : 5602 - 5608
  • [45] Metal-Free Photoredox-Catalyzed Hydrodefluorination of Fluoroarenes Utilizing Amide Solvent as Reductant
    Toriumi, Naoyuki
    Yamashita, Kazuya
    Iwasawa, Nobuharu
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (49) : 12635 - 12641
  • [46] Dual Nucleophilic Substitution Reactions of O,O-Diethyl 2,4-dinitrophenyl Phosphate and Thionophosphate Triesters
    Aguayo, Raul
    Arias, Felipe
    Canete, Alvaro
    Zuniga, Carolina
    Castro, Enrique A.
    Pavez, Paulina
    Santos, Jose G.
    INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 2013, 45 (03) : 202 - 211
  • [47] HYDROLYSIS OF 2,4-DINITROPHENYL PHOSPHATE CATALYZED BY SINGLE-CHAIN, TWIN-TAILED AND BOLAFORM SURFACTANTS
    BUNTON, CA
    DORWIN, EL
    SAVELLI, G
    SI, VC
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1990, 109 (02): : 64 - 69
  • [48] Synthesis and characterisation of transition metal complexes of 2-benzoyl pyridine-2,4-dinitrophenyl hydrazone
    Varghese, Binu
    Jose, Anagha Maria
    Malavika, C. R.
    MATERIALS TODAY-PROCEEDINGS, 2022, 59 : 345 - 351
  • [49] Photoredox-Catalyzed Acylation/Cyclization of 2-Isocyanobiaryls with Oxime Esters for the Synthesis of 6-Acyl Phenanthridines
    Tang, Boxiao
    Ding, Chuan
    Ou, Min
    Liu, Yu
    Liu, Junwei
    Liu, Yilin
    CATALYSTS, 2022, 12 (11)
  • [50] IDENTIFICATION OF METHIONINE-110 AS THE RESIDUE COVALENTLY MODIFIED IN THE ELECTROPHILIC INACTIVATION OF D-AMINO-ACID OXIDASE BY O-(2,4-DINITROPHENYL)HYDROXYLAMINE
    DSILVA, C
    WILLIAMS, CH
    MASSEY, V
    BIOCHEMISTRY, 1987, 26 (06) : 1717 - 1722
12345