Synthesis of Indolo[1,2-a]Quinoxalines via a Pd-Catallyzed Regioselective C-H Olefination/Cyclization Sequence

被引:76
作者
Wang, Liang [1 ]
Guo, Wei [1 ]
Zhang, Xiao-Xiao [1 ]
Xia, Xu-Dong [1 ]
Xiao, Wen-Jing [1 ,2 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
美国国家科学基金会;
关键词
BOND FORMATION; SULFUR YLIDES; CATALYTIC FUNCTIONALIZATION; OXIDATIVE OLEFINATION; AROMATIC-SUBSTITUTION; BIOLOGICAL EVALUATION; DIRECT ARYLATION; BENZOIC-ACIDS; PALLADIUM; CASCADE;
D O I
10.1021/ol203275b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient approach to indolo [1,2-a]quinoxaline derivatives through a Pd-catalyzed regioselective C-H olefination/cyclization sequence has been developed. This transformation has a wide range of substrates with various functional groups, and the corresponding heterocyclic products were obtained in good yields.
引用
收藏
页码:740 / 743
页数:4
相关论文
共 90 条
[81]   Pd(II)-Catalyzed Olefination of sp3 C-H Bonds [J].
Wasa, Masayuki ;
Engle, Keary M. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3680-+
[82]   Ru-catalyzed oxidative coupling of arenes with olefins using O2 [J].
Weissman, H ;
Song, XP ;
Milstein, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (02) :337-338
[83]   Investigating N-methoxy-N′-aryl ureas in oxidative C-H olefination reactions: an unexpected oxidation behaviour [J].
Willwacher, Jens ;
Rakshit, Souvik ;
Glorius, Frank .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (13) :4736-4740
[84]   Palladium-catalyzed oxidative cyclization of N-aryl enamines:: From anilines to indoles [J].
Wuertz, Sebastian ;
Rakshit, Souvik ;
Neumann, Julia J. ;
Droege, Thomas ;
Glorius, Frank .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7230-7233
[85]   Synthesis and antifungal activities of novel 5,6-dihydro-indolo[1,2-a]quinoxaline derivatives [J].
Xu, Hui ;
Fan, Ling-ling .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (05) :1919-1925
[86]   Organopalladium(IV) chemistry [J].
Xu, Ling-Min ;
Li, Bi-Jie ;
Yang, Zhen ;
Shi, Zhang-Jie .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :712-733
[87]   Catalytic coupling of haloolefins with anilides [J].
Zaitsev, VG ;
Daugulis, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4156-4157
[88]   Copper-Catalyzed Direct Benzylation or Allylation of 1,3-Azoles with N-Tosylhydrazones [J].
Zhao, Xia ;
Wu, Guojiao ;
Zhang, Yan ;
Wang, Jianbo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (10) :3296-3299
[89]   N-Acylsulfonamide Assisted Tandem C-H Olefination/Annulation: Synthesis of Isoindolinones [J].
Zhu, Chen ;
Falck, J. R. .
ORGANIC LETTERS, 2011, 13 (05) :1214-1217
[90]   Visible-Light-Induced Oxidation/[3+2] Cycloaddition/Oxidative Aromatization Sequence: A Photocatalytic Strategy To Construct Pyrrolo[2,1-a]isoquinolines [J].
Zou, You-Quan ;
Lu, Liang-Qiu ;
Fu, Liang ;
Chang, Ning-Jie ;
Rong, Jian ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7171-7175