Gold(III)-Catalyzed Tandem Reaction of Ketones with Phenols: Efficient and Highly Selective Synthesis of Functionalized 4H-Chromenes

被引:64
作者
Liu, Yunkui [1 ]
Qian, Jianqiang [1 ]
Lou, Shaojie [1 ]
Zhu, Jie [1 ]
Xu, Zhenyuan [1 ]
机构
[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Zhejiang, Peoples R China
关键词
SALICYL N-TOSYLIMINES; DABCO-CATALYZED REACTION; COMBINATORIAL LIBRARIES; PRIVILEGED STRUCTURES; FACILE CONSTRUCTION; SELF-CONDENSATION; GOLD CATALYSIS; REARRANGEMENT; HETEROCYCLES; 2H-CHROMENES;
D O I
10.1021/jo902619x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and highly selective approach for the synthesis of functionalized 4H-chromenes has been developed via goid(III)-catalyzed condensation/annulation tandem reaction of ketones with phenols.
引用
收藏
页码:1309 / 1312
页数:4
相关论文
共 67 条
[1]   Alternative synthetic methods through new developments in catalysis by gold [J].
Arcadi, Antonio .
CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325
[2]  
BARLUENGA J, 2009, ANGEW CHEM INT EDIT, V15, P8121
[3]   Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists [J].
Behrenswerth, Andrea ;
Volz, Nicole ;
Toraeng, Jakob ;
Hinz, Sonja ;
Braese, Stefan ;
Mueller, Christa E. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (07) :2842-2851
[4]   ANTIINFLAMMATORY MECHANISM OF CORDIACHROMENE-A ACTION [J].
BENSLIMANE, AF ;
POUCHUS, YF ;
VERBIST, JF ;
PETIT, JY ;
BRION, JD ;
WELIN, L .
JOURNAL OF CLINICAL PHARMACOLOGY, 1995, 35 (03) :298-301
[5]   PALLADIUM-CATALYZED CONJUGATE ADDITION TYPE REACTION OF (2-HYDROXYARYL)MERCURY CHLORIDES WITH ALPHA,BETA-UNSATURATED KETONES IN A 2-PHASE SYSTEM - A NEW SYNTHESIS OF 2-CHROMANOLS AND 2-CHROMENES [J].
CACCHI, S ;
MISITI, D ;
PALMIERI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :2995-2999
[6]   Rhodomyrtone, an antibiotic from Rhodomyrtus tomentosa [J].
Dachriyanus ;
Salni ;
Sargent, MV ;
Skelton, BW ;
Soediro, I ;
Sutisna, M ;
White, AH ;
Yulinah, E .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2002, 55 (03) :229-232
[7]  
Dianin A.P., 1914, J. Russ. Phys. Chem. Soc, V36, P1310
[8]   Asymmetric organocatalytic domino reactions [J].
Enders, Dieter ;
Grondal, Christoph ;
Huettl, Matthias R. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581
[9]   Facile construction of functionalized 4H-chromene via tandem benzylation and cyclization [J].
Fan, Jinmin ;
Wang, Zhiyong .
CHEMICAL COMMUNICATIONS, 2008, (42) :5381-5383
[10]   O-arylation versus C-arylation: Copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls [J].
Fang, Yewen ;
Li, Chaozhong .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (17) :6427-6431