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General and Direct Synthesis of 3-Aminoindolizines and Their Analogues via Pd/Cu-Catalyzed Sequential Cross-Coupling/Cycloisomerization Reactions
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Abstract
An efficient and one-step synthesis of 3-aminoindolizines or benz[e]indolizines from the reactions of propargyl amines or amides with heteroaryl bromides was developed. This methodology is realized by a tandem reaction using Pd/Cu catalysts, which could catalyze coupling and cycloisomerization reactions in the same vessel.
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This article has been cited by 8 ACS Journal articles (5 most recent appear below).
Synthesis of Functionalized Indolizines via Copper-Catalyzed Annulation of 2-Alkylazaarenes with α,β-Unsaturated Carboxylic Acids
Yuzhu Yang, Chunsong Xie, Yongju Xie, and Yuhong ZhangOrganic Letters2012 Article ASAPSynthesis of Functionalized Indolizines via Copper-Catalyzed Annulation of 2-Alkylazaarenes with α,β-Unsaturated Carboxylic Acids
Yuzhu Yang, Chunsong Xie, Yongju Xie, and Yuhong ZhangOrganic Letters2012 Article ASAPA novel copper-catalyzed annulation of 2-alkylazaarenes with α,β-unsaturated carboxylic acids has been accomplished. This reaction featuring C–H olefination and decarboxylative amination processes provides a concise access to C-2 arylated indolizines from ...
Experimental and Computational Exploration of Indolizinyl Carbene Generation. A Route to Biindolizines
Inmaculada R. Lahoz, Carlos Silva López, Armando Navarro-Vázquez, and María-Magdalena CidThe Journal of Organic Chemistry2011 Article ASAPExperimental and Computational Exploration of Indolizinyl Carbene Generation. A Route to Biindolizines
Inmaculada R. Lahoz, Carlos Silva López, Armando Navarro-Vázquez, and María-Magdalena CidThe Journal of Organic Chemistry2011 Article ASAPIn previous work, (E)-2-enynyl pyridines were reported to yield indolizinyl singlet carbenes through base-catalyzed E/Z isomerization followed by a 5-exo-dig pseudocoarctate cyclization. We report herein that in the presence of ethyl acrylate these ...
On the Validity of Au-vinylidenes in the Gold-Catalyzed 1,2-Migratory Cycloisomerization of Skipped Propargylpyridines
Yuanzhi Xia, Alexander S. Dudnik, Yahong Li, and Vladimir GevorgyanOrganic Letters2010 12 (23), 5538-5541On the Validity of Au-vinylidenes in the Gold-Catalyzed 1,2-Migratory Cycloisomerization of Skipped Propargylpyridines
Yuanzhi Xia, Alexander S. Dudnik, Yahong Li, and Vladimir GevorgyanOrganic Letters2010 12 (23), 5538-5541A mechanism of the Au-catalyzed cycloisomerization of propargylpyridines has been investigated. Both DFT computational and experimental results strongly support generation of a Au-carbene via a cyclization/proton transfer sequence over the previously ...
Quick Access to Druglike Heterocycles: Facile Silver-Catalyzed One-Pot Multicomponent Synthesis of Aminoindolizines
Yaguang Bai, Jing Zeng, Jimei Ma, Bala Kishan Gorityala, and Xue-Wei LiuJournal of Combinatorial Chemistry2010 12 (5), 696-699Quick Access to Druglike Heterocycles: Facile Silver-Catalyzed One-Pot Multicomponent Synthesis of Aminoindolizines
Yaguang Bai, Jing Zeng, Jimei Ma, Bala Kishan Gorityala, and Xue-Wei LiuJournal of Combinatorial Chemistry2010 12 (5), 696-699A direct and efficient approach to 1-aminoindolizines through three-component one-pot reaction of heteroaryl aldehydes, secondary amines, and terminal alkynes catalyzed by AgBF4 has been developed. Desired products were obtained in moderate to excellent ...
Mechanistic Investigation on the Formation of Indolizines from 2-Enynylpyridines
Inma R. Lahoz, Cristina Sicre, Armando Navarro-Vázquez, Carlos Silva López and María-Magdalena CidOrganic Letters2009 11 (21), 4802-4805Mechanistic Investigation on the Formation of Indolizines from 2-Enynylpyridines
Inma R. Lahoz, Cristina Sicre, Armando Navarro-Vázquez, Carlos Silva López and María-Magdalena CidOrganic Letters2009 11 (21), 4802-48052,3,7-Trisubstituted indolizines were obtained from E- or Z-2-enynyl-4-substituted pyridines. The mechanistic pathway involves a base-catalyzed double-bond isomerization, if the E-isomer is the starting material, followed by a concerted pseudocoarctate ...
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History
- Published In Issue February 01, 2007
- Received November 14, 2006
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