Visible Light-Induced Aerobic Oxyamidation of Indoles: A Photocatalytic Strategy for the Preparation of Tetrahydro-5H-indolo[2,3-b]quinolinols

被引:48
作者
An, Jing [1 ]
Zou, You-Quan [1 ]
Yang, Qing-Qing [1 ]
Wang, Qiang [1 ]
Xiao, Wen-Jing [1 ]
机构
[1] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Coll Chem, Wuhan 430079, Hubei, Peoples R China
基金
美国国家科学基金会;
关键词
aerobic oxidation; indoles; oxyamidation; visible light photocatalysis; PHOTOREDOX CATALYSIS; SINGLET OXYGEN; ORGANIC-SYNTHESIS; PHOTOSENSITIZED OXYGENATION; PENICILLIUM-EXPANSUM; TRYPTOPHAN; OXIDATION; FUNCTIONALIZATION; CYCLOADDITIONS; METABOLITES;
D O I
10.1002/adsc.201300175
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A visible light-induced, aerobic oxyamidation reaction of indoles, using air as the sole oxidant, has been developed. This process serves as a photocatalytic strategy to generate efficiently tetrahydro-5H-indolo[2,3-b]quinolinols, which may have interesting biological and pharmacological activities owing to their privileged indoline structure.
引用
收藏
页码:1483 / 1489
页数:7
相关论文
共 91 条
[11]  
[Anonymous], 2008, ANGEW CHEM INT ED, V47, P9730
[12]  
[Anonymous], 2010, ANGEW CHEM INT ED, P9153
[13]  
[Anonymous], 2008, ANGEW CHEM INT EDIT, DOI 10.1002/ange.200803630
[14]  
[Anonymous], 2012, ANGEW CHEM INT EDIT, V51, P5386
[15]  
[Anonymous], 2008, ANGEW CHEM INT ED, V47, P8170
[16]  
Beaumont S., 2010, Angew. Chem, V122, P1678
[17]  
Benkovics T., 2010, Angew. Chem. Int. Ed, V122, P9339
[18]   Nitrenium ions. Part 3. Acid-catalyzed reactions of 2-tert-butylindole with nitrosoarenes. Crystal structures of 2-tert-butyl-3-p-tolylimino-3H-indole and 3-tert-butyl-3-p-tolylamino-1,3-dihydroindol-2-one [J].
Carloni, P ;
Greci, L ;
Iacussi, M ;
Rossetti, M ;
Cozzini, P ;
Sgarabotto, P .
JOURNAL OF CHEMICAL RESEARCH-S, 1998, (05) :232-+
[19]   Visible light-induced 3-sulfenylation of N-methylindoles with arylsulfonyl chlorides [J].
Chen, Min ;
Huang, Zhi-Tang ;
Zheng, Qi-Yu .
CHEMICAL COMMUNICATIONS, 2012, 48 (95) :11686-11688
[20]   Aerobic Visible-Light Photoredox Radical C-H Functionalization: Catalytic Synthesis of 2-Substituted Benzothiazoles [J].
Cheng, Yannan ;
Yang, Jun ;
Qu, Yue ;
Li, Pixu .
ORGANIC LETTERS, 2012, 14 (01) :98-101