One-Pot Synthesis of Pyrimido[1,6-a]indol-1(2H)-one Derivatives by a Nucleophilic Addition/Cu-Catalyzed N-Arylation/Pd-Catalyzed C-H Activation Sequential Process

被引:70
作者
Wang, Zhi-Jing [1 ]
Yang, Jian-Guo [2 ]
Yang, Fan [1 ]
Bao, Weiliang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
[2] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 317000, Peoples R China
基金
高等学校博士学科点专项科研基金;
关键词
EFFICIENT DOMINO SYNTHESIS; BOND FORMATION; CYCLIZATION CASCADE; COUPLING REACTIONS; MODULAR SYNTHESIS; COPPER; ARYL; INDOLES; FUNCTIONALIZATION; HETEROCYCLES;
D O I
10.1021/ol101041e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and convenient one-pot synthesis of pyrimido[1,6-a]indol-1(2H)-one derivatives through a nucleophilic addition/Cu-catalyzed N-arylation/Pd-catalyzed C H activation sequential process is described. The reaction of easily prepared ortho-gem-dibromovinyl isocyanates with N-alkylanilines gave the desired indole derivatives in moderate to good yields.
引用
收藏
页码:3034 / 3037
页数:4
相关论文
共 74 条
[61]   New synthesis of benzo[b]furan and indole derivatives from 1,1-dibromo-1-alkenes using a tandem Pd-assisted cyclization-coupling reaction [J].
Thielges, S ;
Meddah, E ;
Bisseret, P ;
Eustache, J .
TETRAHEDRON LETTERS, 2004, 45 (05) :907-910
[62]   Synthesis of 2-arylbenzoxazoles by copper-catalyzed intramolecular oxidative C-O coupling of benzanilides [J].
Ueda, Satoshi ;
Nagasawa, Hideko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6411-6413
[63]   A Copper-Catalyzed Tandem Synthesis of Indolo- and Pyrrolo[2,1-a]isoquinolines [J].
Verma, Akhilesh Kumar ;
Kesharwani, Tanay ;
Singh, Jaspal ;
Tandon, Vibha ;
Larock, Richard C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (06) :1138-1143
[64]   Tandem Palladium-Catalyzed N,C-Coupling/Carbonylation Sequence for the Synthesis of 2-Carboxyindoles [J].
Vieira, Tiago O. ;
Meaney, Laura A. ;
Shi, Yong-Ling ;
Alper, Howard .
ORGANIC LETTERS, 2008, 10 (21) :4899-4901
[65]   Copper-catalyzed domino annulation approaches to the synthesis of benzoxazoles under microwave-accelerated and conventional thermal conditions [J].
Viirre, Russell D. ;
Evindar, Ghotas ;
Batey, Robert A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3452-3459
[66]   Assembly of isoquinolines via CuI-catalyzed coupling of β-keto esters and 2-halobenzylamines [J].
Wang, Bao ;
Lu, Biao ;
Jiang, Yongwen ;
Zhang, Yihua ;
Ma, Dawei .
ORGANIC LETTERS, 2008, 10 (13) :2761-2763
[67]   One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling [J].
Watanabe, Toshiaki ;
Ueda, Satoshi ;
Inuki, Shinsuke ;
Oishi, Shinya ;
Fujii, Nobutaka ;
Ohno, Hiroaki .
CHEMICAL COMMUNICATIONS, 2007, (43) :4516-4518
[68]   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
[69]   Copper-catalyzed synthesis of benzimidazoles via cascade reactions of o-haloacetanilide derivatives with amidine hydrochlorides [J].
Yang, Daoshan ;
Fu, Hua ;
Hu, Liming ;
Jiang, Yuyang ;
Zhao, Yufen .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7841-7844
[70]   A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles [J].
Yao, Pei-Yuan ;
Zhang, Yu ;
Hsung, Richard P. ;
Zhao, Kang .
ORGANIC LETTERS, 2008, 10 (19) :4275-4278