Synthesis of Quinolino[3′,4′:4,5] pyrrolo[1,2-f]phenanthridines by Regioselective Sonogashira Reaction Followed by Domino C-N Coupling/Hydroamination/C-H Arylation

被引:9
作者
Ngo Nghia Pham [1 ,2 ,3 ]
Salman, Ghazwan Ali [1 ,4 ]
Ponce, Marian Blanco [1 ]
Tuan Thanh Dang [1 ,3 ]
Spannenberg, Anke [2 ]
Ehlers, Peter [1 ,2 ]
Langer, Peter [1 ,2 ]
机构
[1] Univ Rostock, Inst Chem, Albert Einstein Str 3A, D-18059 Rostock, Germany
[2] Univ Rostock eV, Leibniz Inst Katalyse, Albert Einstein Str 29A, D-18059 Rostock, Germany
[3] VNU Univ Sci Hanoi VNU HUS, Fac Chem, 19 Le Thanh Tong, Hanoi, Vietnam
[4] Univ Al Mustansiriyah, Coll Sci, Dept Chem, Palestine St, Baghdad, Iraq
关键词
Heterocycles; Palladium; Cyclization; Homogeneous catalysis; Domino reactions; COMPLEXES;
D O I
10.1002/ejoc.201700371
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An effective and atom-economic synthesis of quinolino[3',4':4,5] pyrrolo[1,2-f] phenanthridines has been developed. The protocol involves a site-selective Sonogashira reaction of 3,4-dihaloquinoline, followed by a domino C-N coupling/hydroamination/C-H arylation reaction. Quinolino[3',4':4,5]pyrrolo[1,2-f] phenanthridines represent a hitherto unknown class of heterocyclic compounds.
引用
收藏
页码:3865 / 3873
页数:9
相关论文
共 25 条
[1]   Quinine, an old anti-malarial drug in a modern world: role in the treatment of malaria [J].
Achan, Jane ;
Talisuna, Ambrose O. ;
Erhart, Annette ;
Yeka, Adoke ;
Tibenderana, James K. ;
Baliraine, Frederick N. ;
Rosenthal, Philip J. ;
D'Alessandro, Umberto .
MALARIA JOURNAL, 2011, 10
[2]   Heck-like coupling and Pictet-Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines [J].
David, Emilie ;
Pellet-Rostaing, Ephane ;
Lemaire, Marc .
TETRAHEDRON, 2007, 63 (36) :8999-9006
[3]   Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor [J].
Fandrick, Keith R. ;
Li, Wenjie ;
Zhang, Yongda ;
Tang, Wenjun ;
Gao, Joe ;
Rodriguez, Sonia ;
Patel, Nitinchandra D. ;
Reeves, Diana C. ;
Wu, Jiang-Ping ;
Sanyal, Sanjit ;
Gonnella, Nina ;
Qu, Bo ;
Haddad, Nizar ;
Lorenz, Jon C. ;
Sidhu, Kanwar ;
Wang, June ;
Ma, Shengli ;
Grinberg, Nelu ;
Lee, Heewon ;
Tsantrizos, Youla ;
Poupart, Marc-Andre ;
Busacca, Carl A. ;
Yee, Nathan K. ;
Lu, Bruce Z. ;
Senanayake, Chris H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :7144-7148
[4]   Remarkable stability of tetrabenzo[a, c, g, i]fluorenyl ammonium salts in water: syntheses, reactions, and crystal structures [J].
Frey, Okko N. ;
Stalling, Timo ;
Schlueter, Florian ;
Saak, Wolfgang ;
Schmidtmann, Marc ;
Haase, Detlev ;
Beckhaus, Ruediger .
DALTON TRANSACTIONS, 2016, 45 (03) :1085-1092
[5]   Novel 1H-Pyrrolo[3,2-c]quinoline Based 5-HT6 Receptor Antagonists with Potential Application for the Treatment of Cognitive Disorders Associated with Alzheimer's Disease [J].
Grychowska, Katarzyna ;
Satala, Grzegorz ;
Kos, Tomasz ;
Partyka, Anna ;
Colacino, Evelina ;
Chaumont-Dubel, Severine ;
Bantreil, Xavier ;
Wesolowska, Anna ;
Pawlowski, Maciej ;
Martinez, Jean ;
Marin, Philippe ;
Subra, Gilles ;
Bojarski, Andrzej J. ;
Lamaty, Frederic ;
Popik, Piotr ;
Zajdel, Pawel .
ACS CHEMICAL NEUROSCIENCE, 2016, 7 (07) :972-983
[6]   Phenylquinoline Derivatives as Efficient Interfacial Layer Materials for High-Performance Organic Electronic Devices [J].
Gunasekar, Kumarasamy ;
Cho, Woosum ;
Long, Dang Xuan ;
Reddy, Saripally Sudhaker ;
Song, Myungkwan ;
Noh, Yong-Young ;
Jin, Sung-Ho .
ADVANCED ELECTRONIC MATERIALS, 2016, 2 (08)
[7]   Synthesis of Polycyclic-fused Heterocycles Combining Both Quinoline Ring and Benzoxepine Framework in A Single Molecule [J].
Li, Yang ;
Lin, Guihai ;
Gao, Wentao .
POLYCYCLIC AROMATIC COMPOUNDS, 2012, 32 (04) :469-486
[8]  
Mahajan P., J HETEROCYCL CHEM
[9]   Quinoline: A versatile heterocyclic [J].
Marella, Akranth ;
Tanwar, Om Prakash ;
Saha, Rikta ;
Ali, Mohammad Rahmat ;
Srivastava, Sandeep ;
Akhter, Mymoona ;
Shaquiquzzaman, Mohammad ;
Alam, Mohammad Mumtaz .
SAUDI PHARMACEUTICAL JOURNAL, 2013, 21 (01) :1-12
[10]   Synthesis of Quinoline-Fused 1-Benzazepines through a Mannich-Type Reaction of a C,N-Bisnucleophile Generated from 2-Aminobenzaldehyde and 2-Methylindole [J].
Min, Lijun ;
Pan, Bin ;
Gu, Yanlong .
ORGANIC LETTERS, 2016, 18 (03) :364-367