Access to Isoquinolin-1(2H)-ones and Pyridones by Cobalt-Catalyzed Oxidative Annulation of Amides with Allenes

被引:50
作者
Boobalan, Ramadoss [1 ]
Kuppusamy, Ramajayam [1 ]
Santhoshkumar, Rajagopal [1 ]
Gandeepan, Parthasarathy [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
allenes; amides; annulation; C-H activation; cobalt; C-H ACTIVATION; BOND FORMATION; SELECTIVE ACCESS; TERMINAL ALKYNES; ATOM ECONOMY; PALLADIUM; FUNCTIONALIZATION; CYCLIZATION; ARENES; OPPORTUNITIES;
D O I
10.1002/cctc.201601190
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A cobalt-catalyzed oxidative annulation of amides with allenes to provide isoquinolin-1(2H)-ones and pyridones was explored. The new catalytic reaction proceeded through aminoquinolinedirected C-H activation followed by unusual regioselective insertion, annulation, and isomerization. A variety of functionalized amides and allenes were converted into the corresponding products under mild reaction conditions.
引用
收藏
页码:273 / 277
页数:5
相关论文
共 95 条
[1]   Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond [J].
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8948-8954
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   The conversion of allenes to strained three-membered heterocycles [J].
Adams, C. S. ;
Weatherly, C. D. ;
Burke, E. G. ;
Schomaker, J. M. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (09) :3136-3163
[4]   Ketenes and Other Cumulenes as Reactive Intermediates [J].
Allen, Annette D. ;
Tidwell, Thomas T. .
CHEMICAL REVIEWS, 2013, 113 (09) :7287-7342
[5]  
Anastas PT, 1996, ACS SYM SER, V626, P1
[6]  
[Anonymous], 2012, ANGEW CHE, DOI DOI 10.1002/ANGE.201201273
[7]  
[Anonymous], 2016, ANGEW CHE
[8]  
[Anonymous], 2013, ANGEW CHEM-GER EDIT
[9]  
[Anonymous], 2015, Angew. Chem.
[10]  
[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201301451