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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 17
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Original Articles

Low-Valent Titanium Induced Reductive Coupling of Nitriles with Nitro Compounds

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Pages 3249-3262 | Received 11 Mar 1998, Published online: 23 Aug 2006

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Richard J. Fox, Nicolas L. Cuniere, Lopa Bakrania, Carolyn Wei, Neil A. Strotman, Michael Hay, Dayne Fanfair, Christopher Regens, Gregory L. Beutner, Michael Lawler, Paul Lobben, Maxime C. Soumeillant, Benjamin Cohen, Keming Zhu, Dimitri Skliar, Thorsten Rosner, Chester E. Markwalter, Yi Hsiao, Kristy Tran & Martin D. Eastgate. (2018) C–H Arylation in the Formation of a Complex Pyrrolopyridine, the Commercial Synthesis of the Potent JAK2 Inhibitor, BMS-911543. The Journal of Organic Chemistry 84:8, pages 4661-4669.
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Meng Li, Jia Zheng, Weigao Hu, Chunsheng Li, Jianxiao Li, Songjia Fang, Huanfeng Jiang & Wanqing Wu. (2018) Palladium-Catalyzed Cyclization of N -Acyl- o -alkynylanilines with Isocyanides Involving a 1,3-Acyl Migration: Rapid Access to Functionalized 2-Aminoquinolines . Organic Letters 20:22, pages 7245-7248.
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Wanqing Wu, Meng Li, Jia Zheng, Weigao Hu, Chunsheng Li & Huanfeng Jiang. (2018) Tandem cyclization of o -alkynylanilines with isocyanides triggered by intramolecular nucleopalladation: access to heterocyclic fused 2-aminoquinolines . Chemical Communications 54:50, pages 6855-6858.
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Pei Xu, Tong-Hao Zhu, Tian-Qi Wei, Shun-Yi Wang & Shun-Jun Ji. (2016) Co(acac) 2 /O 2 -catalyzed oxidative isocyanide insertion with 2-vinylanilines: efficient synthesis of 2-aminoquinolines . RSC Advances 6:39, pages 32467-32470.
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Umesh D. Patil & Pramod P. Mahulikar. (2012) A Convenient, TiCl 4 /SnCl 4 -Mediated Synthesis of N -Phenyl or N -Aryl Benzamidines and N -Phenylpicolinamidines . ISRN Organic Chemistry 2012, pages 1-6.
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E. V. Kuvaeva, E. V. Fedorova, V. V. Zaitsev, I. P. Yakovlev, V. I. Zakharov & T. L. Semakova. (2012) Synthesis and structure of aroylamidines and N-arylbenzamidines hydrochlorides. Russian Journal of Organic Chemistry 48:2, pages 209-213.
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Takashi Tomioka, Yusuke Takahashi & Toshihide Maejima. (2012) One-pot synthesis of 2-aminoquinoline-based alkaloids from acetonitrile. Organic & Biomolecular Chemistry 10:26, pages 5113.
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Stéphane Caron, Lulin Wei, Jasmin Douville & Arun Ghosh. (2010) Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Synthesis of Amidines. The Journal of Organic Chemistry 75:3, pages 945-947.
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P.A. Keller. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 217 308 .
Yun-kui Liu, Dan-qian Xu, Zhen-yuan Xu & Yong-min Zhang. (2007) Sm/TiCl4 (cat.) system-mediated intermolecular and intramolecular reductive coupling reactions of ketones with esters. Journal of Zhejiang University-SCIENCE A 8:7, pages 999-1003.
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Vadim Yu. Kukushkin & Armando J. L. Pombeiro. (2002) Additions to Metal-Activated Organonitriles. Chemical Reviews 102:5, pages 1771-1802.
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Zhi‐Fang Li & Yong‐Min Zhang. (2010) Low‐valent Titanium Induced Reductive Coupling of O ‐Nitrophenylazide with Benzoyl Substituted Ketene Dithioacetals: a Novel Synthesis of 4‐Aryl‐2‐methylthio‐3Z7‐l,5‐benzodiazepines . Chinese Journal of Chemistry 19:10, pages 996-998.
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Yongmin Ma & Yongmin Zhang. (2019) Synthesis of Quinolines: Reductive Coupling Reactions of 2-nitro-1,3-diphenyl-2-propen-1-one induced by low-valent titanium. Journal of Chemical Research 2001:3, pages 108-109.
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Yong‐Min Zhang, Wei‐Hui Zhong & Xiao‐Yian Chen. (2010) Low‐Valent Titanium Induced Simultaneous Reduction of Nitro Group and SS Bond in Nitrodisulfides: A Facile Synthesis of 2 H ‐1,4‐Benzothiazines . Chinese Journal of Chemistry 19:2, pages 189-192.
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Weihui Zhong, Yongmin Zhang & Xiaoyuan Chen. (2001) Simultaneous reduction of the nitro group and the azide group in o -nitrophenylazide induced by the TiCl 4 /Sm system: a novel synthesis of 2,3-dihydro-1 H -1,5-benzodiazepines. Tetrahedron Letters 42:1, pages 73-75.
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Wei‐Hui Zhong, Xiao‐Yuan Chen & Yong‐Min Zhang. (2010) Low‐valent titanium induced reductive cyclization of nitro compounds and aliphatic ketones: facile synthesis of 3, 4‐dihydro(2 H ) ‐ 1, 2, 4‐benzothiadiazine‐1, 1‐dioxides . Chinese Journal of Chemistry 18:5, pages 786-788.
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Yongmin Ma & Yongmin Zhang. (2019) A Novel reduction of O-Nitrophenoxy Compounds Promoted by Low-Valent Titanium: An Access to 2H-1,4-Benzoxazine Derivatives. Journal of Chemical Research 2000:8, pages 388-389.
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Xiaoyuan Chen, Weihui Zhong & Yongmin Zhang. (2019) A New Route to 2,3-Dihydro-1,5-Benzothiazepines from Nitrodisulfides and α,β-Unsaturated Ketones by Smi 2 . Journal of Chemical Research 2000:8, pages 386-387.
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Robert D. Larsen & Ian W. Davies. 1999. A Critical Review of the 1998 Literature preceded by two Chapters on Current Heterocyclic Topics. A Critical Review of the 1998 Literature preceded by two Chapters on Current Heterocyclic Topics 230 255 .
L. ZHOU & Y. ZHANG. (2010) ChemInform Abstract: Low‐Valent Titanium Induced Reductive Coupling of Nitriles with Nitro Compounds.. ChemInform 29:49.
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