Pd-Catalyzed Tandem Cyclization via C-H Arylation and Acylation for the Construction of Polycyclic Scaffolds

被引:33
作者
Mu, Bing [1 ,2 ,3 ]
Li, Jingya [4 ]
Zou, Dapeng [1 ]
Wu, Yusheng [1 ,4 ]
Chang, Junbiao [1 ]
Wu, Yangjie [1 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Peoples R China
[2] Zhengzhou Normal Univ, Coll Chem & Chem Engn, Zhengzhou 450044, Peoples R China
[3] Huanghe Sci & Technol Coll, Sch Med, Zhengzhou 450000, Peoples R China
[4] Tetranov Biopharm LLC, Zhengzhou 450052, Peoples R China
关键词
DIRECT ACCESS; FUNCTIONALIZATION; ALKYNES; RHODIUM; DERIVATIVES; ANNULATION; ANALOGS; ARYL; ACTIVATION; ALDEHYDES;
D O I
10.1021/acs.orglett.6b02571
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first Pd-catalyzed tandem cyclization of imidazo[1,2-a]pyridines with 2-chlorobenzaldehydes through C-H arylation and acylation is presented for the efficient synthesis of novel 6H-benzo[b]imidazo[5,1,2-de]quinolizin-6-ones. The direct acylation reaction proceeded smoothly without the aid of directing groups and in the presence of air as a clean and free terminal oxidant.
引用
收藏
页码:5260 / 5263
页数:4
相关论文
共 56 条
[1]   DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].
ALMIRANTE, L ;
POLO, L ;
MUGNAINI, A ;
PROVINCIALI, E ;
RUGARLI, P ;
BIANCOTTI, A ;
GAMBA, A ;
MURMANN, W .
JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+
[2]  
Andaloussi M, 2005, HETEROCYCLES, V65, P1071
[3]   Synthesis of imidazo[1,2-a]pyridines: a decade update [J].
Bagdi, Avik Kumar ;
Santra, Sougata ;
Monir, Kamarul ;
Hajra, Alakananda .
CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575
[4]   Copper(I)-mediated preparation of new pyrano[3′,4′:4,5]imidazo[1,2-a]pyridin-1-one compounds under mild palladium-free conditions [J].
Bahlaouan, Zineb ;
Abarbri, Mohamed ;
Duchene, Alain ;
Thibonnet, Jerome ;
Henry, Nicolas ;
Enguehard-Gueiffier, Cecile ;
Gueiffier, Alain .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (04) :1212-1218
[5]   Palladium-Catalyzed ortho-Aroylation of 2-Arylbenzothiazoles and 2-Arylbenzoxazoles with Aldehydes [J].
Banerjee, Arghya ;
Santra, Sourav Kumar ;
Guin, Srimanta ;
Rout, Saroj Kumar ;
Patel, Bhisma K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (07) :1367-1376
[6]   Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes [J].
Basle, Olivier ;
Bidange, Johan ;
Shuai, Qi ;
Li, Chao-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) :1145-1149
[7]   Highly regioselective C-H bond functionalization: palladium-catalyzed arylation of substituted imidazo[1,2-a]pyridine with aryl chlorides [J].
Cao, Hua ;
Lin, Yuanguang ;
Zhan, Haiying ;
Du, Zuodong ;
Lin, Xiulian ;
Liang, Qi-Mei ;
Zhang, Hong .
RSC ADVANCES, 2012, 2 (14) :5972-5975
[8]   Anthraquinones with quinone reductase-inducing activity and Benzophenones from Morinda citrifolia (Noni) roots [J].
Deng, Ye ;
Chin, Young-Won ;
Chai, Heebyung ;
Keller, William J. ;
Kinghorn, A. Douglas .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (12) :2049-2052
[9]   Probing nanocavities with proton-transfer fluorescence [J].
Douhal, A ;
AmatGuerri, F ;
Acuna, AU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1514-1516
[10]   Palladium-catalyzed benzo[d]isoxazole synthesis by C-H activation/[4+1] annulation [J].
Duan, Pingping ;
Yang, Yunfang ;
Ben, Rong ;
Yan, Yiyong ;
Dai, Lu ;
Hong, Mei ;
Wu, Yun-Dong ;
Wang, Dongqi ;
Zhang, Xinhao ;
Zhao, Jing .
CHEMICAL SCIENCE, 2014, 5 (04) :1574-1578