Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones

被引：40

作者：

Aganda, Kim Christopher C. ^{[1
,3
]}

Hong, Boseok ^{[2
]}

Lee, Anna ^{[3
]}

机构：

[1] Myongji Univ, Dept Energy Sci & Technol, Yongin 17058, South Korea

[2] Myongji Univ, Dept Chem, Yongin 17058, South Korea

[3] Jeonbuk Natl Univ, Dept Chem, Jeonju 54896, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 05期

基金：

新加坡国家研究基金会;

关键词：

quinoxalin-2(1H)-ones; visible light; photo catalysis; radical reactions; selective synthesis; SINGLET OXYGEN; DECARBOXYLATIVE ACYLATION; PHOTOSENSITIZED OXIDATION; PHOTOREDOX CATALYSIS; METAL; DESIGN; FUNCTIONALIZATION; QUINOXALINONES; INHIBITORS; SULFOXIDES;

D O I：

10.1002/adsc.202001396

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores.

引用

页码：1443 / 1448

页数：6

共 60 条

[1] Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis [J].

Afewerki, Samson ;

Cordova, Armando .

CHEMICAL REVIEWS, 2016, 116 (22) :13512-13570

[2] Visible-light-mediated direct C3-arylation of 2H-indazoles enabled by an electron-donor-acceptor complex [J].

Aganda, Kim Christopher C. ;

Kim, Junyoung ;

Lee, Anna .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (45) :9698-9702

[3] Aerobic α-Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo-photocatalysis [J].

Aganda, Kim Christopher C. ;

Hong, Boseok ;

Lee, Anna .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :1124-1129

[4] Reaction of phenol with singlet oxygen [J].

Al-Nu'airat, Jomana ;

Dlugogorski, Bogdan Z. ;

Gao, Xiangpeng ;

Zeinali, Nassim ;

Skut, Jakub ;

Westmoreland, Phillip R. ;

Oluwoye, Ibukun ;

Altarawneh, Mohammednoor .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2019, 21 (01) :171-183

[5] Photosensitized oxidation of alkyl phenyl sulfoxides. C-S bond cleavage in alkyl phenyl sulfoxide radical cations [J].

Baciocchi, Enrico ;

Del Giacco, Tiziana ;

Lanzalunga, Osvaldo ;

Mencarelli, Paolo ;

Procacci, Barbara .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :5675-5682

[6] Sodium azide as a specific quencher of singlet oxygen during chemiluminescent detection by luminol and Cypridina luciferin analogues [J].

Bancirova, Martina .

LUMINESCENCE, 2011, 26 (06) :685-688

[7] Visible-light-promoted acridine red catalyzed aerobic oxidative decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones [J].

Bao, Pengli ;

Liu, Fei ;

Lv, Yufen ;

Yue, Huilan ;

Li, Jiang-Sheng ;

Wei, Wei .

ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (03) :492-498

[8]

Beutner S, 2000, METHOD ENZYMOL, V319, P226

[9] Visible-Light-Mediated Oxygenation Reactions using Molecular Oxygen [J].

Bian, Changliang ;

Singh, Atul K. ;

Niu, Linbin ;

Yi, Hong ;

Lei, Aiwen .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) :386-396

[10] THE QUENCHING OF FLUORESCENCE - DEVIATIONS FROM THE STERN VOLMER LAW [J].

BOAZ, H ;

ROLLEFSON, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (08) :3435-3443

← 1 2 3 4 5 6 →