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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 24
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Original Articles

Substituted 8-Methoxyquinolines: Regioselective Bromination, Coupling Reactions and Cyclization to an 11H-Indolo[3,2-C]quinoline

Francois Trécourt Laboratoire de Chimie Organique Fine et Hétérocyclique de l′IRCOF, URA CNRS 1429 Institut National des Sciences Appliquées de Rouen, BP 08, 76131, Mont-Saint-Aignan, Cedex, France
,
Florence Mongin Laboratoire de Chimie Organique Fine et Hétérocyclique de l′IRCOF, URA CNRS 1429 Institut National des Sciences Appliquées de Rouen, BP 08, 76131, Mont-Saint-Aignan, Cedex, France
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Marc Mallet Laboratoire de Chimie Organique Fine et Hétérocyclique de l′IRCOF, URA CNRS 1429 Institut National des Sciences Appliquées de Rouen, BP 08, 76131, Mont-Saint-Aignan, Cedex, France
&
Guy Quéguiner Laboratoire de Chimie Organique Fine et Hétérocyclique de l′IRCOF, URA CNRS 1429 Institut National des Sciences Appliquées de Rouen, BP 08, 76131, Mont-Saint-Aignan, Cedex, France
Pages 4011-4024 | Received 06 Apr 1995, Published online: 23 Sep 2006

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D. Csányi, G. Timári & Gy. Hajós. (1999) An Alternative Synthesis of Quindoline and one of its Closely Related Derivatives. Synthetic Communications 29:22, pages 3959-3969.
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Articles from other publishers (29)

Mohamed Hasyeoui, Frédéric Lassagne, William Erb, Manal Nael, Khaled M. Elokely, Apirat Chaikuad, Stefan Knapp, Adrian Jorda, Soraya L. Vallés, Emie Quissac, Maïté Verreault, Thomas Robert, Stéphane Bach, Ali Samarat & Florence Mongin. (2023) Oxazolo[5,4-f]quinoxaline-type selective inhibitors of glycogen synthase kinase-3α (GSK-3α): Development and impact on temozolomide treatment of glioblastoma cells. Bioorganic Chemistry 134, pages 106456.
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Ümit Muhammet Koçyiğit, Salih Ökten, Osman Çakmak, Gizem Burhan, Mehmet Ataş, Parham Taslimi & İlhami Gülçin. (2022) Arylated Quinoline and Tetrahydroquinolines: Synthesis, Characterization and Their Metabolic Enzyme Inhibitory and Antimicrobial Activities. ChemistrySelect 7:37.
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Elida N. Thobokholt, Enrique L. Larghi, Andrea B. J. Bracca & Teodoro S. Kaufman. (2020) Isolation and synthesis of cryptosanguinolentine (isocryptolepine), a naturally-occurring bioactive indoloquinoline alkaloid. RSC Advances 10:32, pages 18978-19002.
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Rodisnel Perdomo Rivera, Peter Ehlers, Eugenio Torres Rodríguez & Peter Langer. (2018) Synthesis of 7 H -Indolo[2,3- c ]quinolines by Chemoselective Suzuki Reaction Followed by a Ring-Closing Two-Fold Buchwald-Hartwig Reaction of 3-Bromo-4-iodoquinoline . ChemistrySelect 3:40, pages 11177-11179.
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Ngo Nghia Pham, Sophie Janke, Ghazwan Ali Salman, Tuan Thanh Dang, Thanh Son Le, Anke Spannenberg, Peter Ehlers & Peter Langer. (2017) Convenient Synthesis of 11-Substituted 11 H -Indolo[3,2- c ]quinolines by Sequential Chemoselective Suzuki Reaction/Double C-N Coupling . European Journal of Organic Chemistry 2017:37, pages 5554-5565.
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Osman Çakmak & Salih Ökten. (2017) Regioselective bromination: Synthesis of brominated methoxyquinolines. Tetrahedron 73:36, pages 5389-5396.
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William F. Berkowitz & Stuart W. McCombie. 2004. Organic Reactions. Organic Reactions 1 170 .
Victor Snieckus & Eric J.‐G. Anctil. 2014. Metal‐Catalyzed Cross‐Coupling Reactions and More. Metal‐Catalyzed Cross‐Coupling Reactions and More 1067 1133 .
Savitha Gurunathan & Paramasivam Thirumalai Perumal. (2011) Synthesis of novel 3-bromo-1,2-dihydroquinolines via palladium mediated intramolecular cyclization of N-tosyl-N-propargyl anilines. Tetrahedron Letters 52:15, pages 1783-1787.
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Robert M. Gengan, Pitchai Pandian, Chandraprakash Kumarsamy & Palathurai S. Mohan. (2010) Convenient and Efficient Microwave-Assisted Synthesis of a Methyl Derivative of the Fused Indoloquinoline Alkaloid Cryptosanguinolentine. Molecules 15:5, pages 3171-3178.
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Xiaoxia Zhang, Tuanli Yao, Marino A. Campo & Richard C. Larock. (2010) Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines. Tetrahedron 66:6, pages 1177-1187.
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Dalip Kumar, Maruthi Kumar. N.V. S. Rao. (2009) A Facile and Expeditious Synthesis of Cryptosanguinolentines. Chemistry Letters 38:2, pages 156-157.
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Emilie David, Stéphane Pellet-Rostaing & Marc Lemaire. (2007) Heck-like coupling and Pictet–Spengler reaction for the synthesis of benzothieno[3,2-c]quinolines. Tetrahedron 63:36, pages 8999-9006.
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Nadia M. Ahmad. 2007. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist 511 539 .
Gordon W. Gribble. 2007. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist. Palladium in Heterocyclic Chemistry - A Guide for the Synthetic Chemist 81 188 .
T. Dhanabal, R. Sangeetha & P.S. Mohan. (2006) Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives. Tetrahedron 62:26, pages 6258-6263.
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Anshu Dandia, Kapil Arya & Nidhi Dhaka. (2019) Multistep Microwave Assisted Solvent Free Green Chemical Synthesis of 2,7-Dihydro-3 H -Pyridazino[3′,4′:4,5]Indolo[3,2- c ]Quinoline-3,13(12 H )-Dione . Journal of Chemical Research 2006:3, pages 192-198.
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Kazuhiro Kobayashi, Yusuke Izumi, Kazutaka Hayashi, Osamu Morikawa & Hisatoshi Konishi. (2005) Synthesis of 11 H -Indolo[3,2- c ]quinoline Derivatives Carrying a Substituent at the 6-Position . Bulletin of the Chemical Society of Japan 78:12, pages 2171-2174.
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T. Dhanabal, R. Sangeetha & P.S. Mohan. (2005) Fischer indole synthesis of the indoloquinoline alkaloid: cryptosanguinolentine. Tetrahedron Letters 46:26, pages 4509-4510.
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Xiaoxia Zhang, Marino A. Campo, Tuanli Yao & Richard C. Larock. (2005) Synthesis of Substituted Quinolines by Electrophilic Cyclization of N -(2-Alkynyl)anilines . Organic Letters 7:5, pages 763-766.
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Steven Hostyn, Bert U.W. Maes, Luc Pieters, Guy L.F. Lemière, Péter Mátyus, György Hajós & Roger A. Dommisse. (2005) Synthesis of the benzo-β-carboline isoneocryptolepine: the missing indoloquinoline isomer in the alkaloid series cryptolepine, neocryptolepine and isocryptolepine. Tetrahedron 61:6, pages 1571-1577.
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Eric J.‐G. Anctil & Victor Snieckus. 2004. Metal‐Catalyzed Cross‐Coupling Reactions. Metal‐Catalyzed Cross‐Coupling Reactions 761 813 .
Nadia M. Ahmad & Jie Jack Li. 2003. 1 30 .
Mariann Béres, Géza Timári & György Hajós. (2002) Straightforward synthesis of 11H-indolo[3,2-c]isoquinoline and benzofuro[3,2-c]isoquinoline by ring transformation. Tetrahedron Letters 43:34, pages 6035-6038.
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R.Nandha Kumar, T. Suresh & P.S. Mohan. (2002) A photochemical route to synthesize cryptosanguinolentine. Tetrahedron Letters 43:18, pages 3327-3328.
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. 2000. Palladium in heterocyclic chemistry - A guide for the synthetic chemist. Palladium in heterocyclic chemistry - A guide for the synthetic chemist 73 181 .
Tibor Soós, Géza Timári & György Hajós. (1999) A concise synthesis of furostifoline. Tetrahedron Letters 40:49, pages 8607-8609.
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Louis S. Hegedus. (1997) Transition metals in organic synthesis. Highlights for the year 1995. Coordination Chemistry Reviews 161, pages 129-255.
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F. TRECOURT, F. MONGIN, M. MALLET & G. QUEGUINER. (2010) ChemInform Abstract: Substituted 8‐Methoxyquinolines: Regioselective Bromination, Coupling Reactions and Cyclization to an 11H‐Indolo(3,2‐c)quinoline.. ChemInform 27:16.
Crossref

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