Palladium-catalyzed cascade reactions of coumarins with alkynes: synthesis of highly substituted cyclopentadiene fused chromones

被引:28
作者
Wang, Lei [1 ]
Peng, Shiyong [1 ]
Wang, Jian [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
C-H ACTIVATION; INTERNAL ALKYNES; FLAVONOIDS; ARYLATION; ANNULATION; MULTIPLE; ACIDS;
D O I
10.1039/c1cc10939a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The coupling of coumarins with alkynes is described, which proceeds through a palladium-catalyzed cascade sequence. This process provides a new route to the synthesis of highly substituted cyclopentadiene fused chromones.
引用
收藏
页码:5422 / 5424
页数:3
相关论文
共 47 条
[11]   Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity [J].
Giri, Ramesh ;
Shi, Bing-Feng ;
Engle, Keary M. ;
Maugel, Nathan ;
Yu, Jin-Quan .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3242-3272
[12]   HIV-inhibitory prenylated xanthones and flavones from Maclura tinctoria [J].
Groweiss, A ;
Cardellina, JH ;
Boyd, MR .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11) :1537-1539
[13]   Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes [J].
Guimond, Nicolas ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12050-+
[14]   Rh(I)-catalyzed carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids leading to indenones [J].
Harada, Yasuyuki ;
Nakanishi, Jun ;
Fujihara, Hirokazu ;
Tobisu, Mamoru ;
Fukumoto, Yoshiya ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5766-5771
[15]  
Harvey R. G., 1997, POLYCYCLIC AROMATIC
[16]   The combinatorial synthesis of bicyclic privileged structures or privileged substructures [J].
Horton, DA ;
Bourne, GT ;
Smythe, ML .
CHEMICAL REVIEWS, 2003, 103 (03) :893-930
[17]  
HOULT JRS, 1994, METHOD ENZYMOL, V234, P443
[18]   O-Dihaloarenes as aryne precursors for nickel-catalyzed [2+2+2]cycloaddition with alkynes and nitriles [J].
Hsieh, Jen-Chieh ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2008, (26) :2992-2994
[19]   Pd-catalyzed reactions of o-diiodoarenes with alkynes for aromatic ring extension [J].
Huang, WY ;
Zhou, X ;
Kanno, K ;
Takahashi, T .
ORGANIC LETTERS, 2004, 6 (14) :2429-2431
[20]   Exploiting Substituent Effects for the Synthesis of a Photooxidatively Resistant Heptacene Derivative [J].
Kaur, Irvinder ;
Stein, Nathan N. ;
Kopreski, Ryan P. ;
Miller, Glen P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) :3424-+