Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)-ones with Arylboronic Acids

被引：175
作者：
Carrer, Amandine [1 ]
Brion, Jean-Daniel [1 ]
Messaoudi, Samir [1 ]
Alami, Mouad [1 ]
机构：
[1] Univ Paris 11, CNRS, BioCIS UMR 8076, LabEx LERMIT,Lab Chim Therapeut,Fac Pharm, F-92296 Chatenay Malabry, France
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 21期
关键词：
C-H FUNCTIONALIZATION; CATALYZED DIRECT ARYLATION; COUPLING REACTIONS; SITE-SELECTIVITY; BOND ARYLATIONS; HALOGENATION; ENAMINONES; ACCESS; FACILE;
D O I：
10.1021/ol4028946
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward palladium-catalyzed oxidative C-3 arylation of quinoxalin-2(1H)-ones with arylboronic acids is reported. This protocol is compatible with a wide range of functional groups and allows construction of various biologically important quinoxalin-2(1H)-one backbones.
引用
收藏
页码：5606 / 5609
页数：4
相关论文
共 55 条
[1]   Ruthenium-Catalyzed Direct C-H Bond Arylations of Heteroarenes [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2011, 13 (13) :3332-3335
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[4]   Innate and Guided C-H Functionalization Logic [J].
Brueckl, Tobias ;
Baxter, Ryan D. ;
Ishihara, Yoshihiro ;
Baran, Phil S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :826-839
[5]   Synthesis of 3,4-Disubstituted Quinolin-2-(1H)-ones via Palladium-Catalyzed Decarboxylative Arylation Reactions [J].
Carrer, Amandine ;
Brion, Jean-Daniel ;
Messaoudi, Samir ;
Alami, Mouad .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (10) :2044-2054
[6]   Quinoline tricyclic derivatives. Design, synthesis and evaluation of the antiviral activity of three new classes of RNA-dependent RNA polymerase inhibitors [J].
Carta, Antonio ;
Briguglio, Irene ;
Piras, Sandra ;
Corona, Paola ;
Boatto, Giampiero ;
Nieddu, Maria ;
Giunchedi, Paolo ;
Marongiu, Maria Elena ;
Giliberti, Gabriele ;
Iuliano, Filippo ;
Blois, Sylvain ;
Ibba, Cristina ;
Busonera, Bernardetta ;
La Colla, Paolo .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (23) :7070-7084
[7]  
Deb A., 2013, EUR J ORG CHEM, P5208
[8]   Impact of Substituents on the Isatin Ring on the Reaction Between Isatins with Ortho-Phenylenediamine [J].
Dowlatabadi, Reza ;
Khalaj, Ali ;
Rahimian, Sima ;
Montazeri, Maedeh ;
Amini, Mohsen ;
Shahverdi, Ahmadreza ;
Mahjub, Elham .
SYNTHETIC COMMUNICATIONS, 2011, 41 (11) :1650-1658
[9]  
Funk P., 2013, ACS COMB SCI, V15, P20
[10]   Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates [J].
Ge, Haibo ;
Niphakis, Micah J. ;
Georg, Gunda I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (12) :3708-+
123456