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Gold-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions or in Water
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Abstract
A gold(III)-catalyzed multicomponent coupling/cycloisomerization reaction of heteroaryl aldehydes, amines, and alkynes under solvent-free conditions or in water has been developed. This methodology provides rapid access to substituted aminoindolizines with high atom economy and high catalytic efficiency. Especially, the coupling of enantiomerically enriched amino acid derivatives produces the corresponding N-indolizine-incorporated amino acid derivatives without loss of enantiomeric purity.
Citing Articles
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This article has been cited by 23 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 ...
The Role of Gold Acetylides as a Selectivity Trigger and the Importance of gem-Diaurated Species in the Gold-Catalyzed Hydroarylating-Aromatization of Arene-Diynes
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A. Stephen K. Hashmi, Ingo Braun, Matthias Rudolph, and Frank RomingerOrganometallics2012 31 (2), 644-661Terminal 1,2-dialkynylarenes undergo an unexpected cyclization hydroarylation reaction toward naphthalene derivatives in benzene as the solvent. The regioselectivity of the reaction can be controlled by careful catalyst tuning. Also, the preparation of a ...
Synthesis of Propargylic and Allenic Carbamates via the C–H Amination of Alkynes
R. David Grigg, Jared W. Rigoli, Simon D. Pearce, and Jennifer M. SchomakerOrganic Letters2012 14 (1), 280-283Synthesis of Propargylic and Allenic Carbamates via the C–H Amination of Alkynes
R. David Grigg, Jared W. Rigoli, Simon D. Pearce, and Jennifer M. SchomakerOrganic Letters2012 14 (1), 280-283Propargylic amines are important intermediates for the synthesis of nitrogen-containing heterocycles. The insertion of a nitrene into a propargylic C–H bond has not been explored, despite the attention directed toward the Rh-catalyzed amination of other ...
Gold-Catalyzed Three-Component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles from Alkynes, Hydrazines, and Aldehydes or Ketones
Yamato Suzuki, Saori Naoe, Shinya Oishi, Nobutaka Fujii, and Hiroaki OhnoOrganic Letters2012 14 (1), 326-329Gold-Catalyzed Three-Component Annulation: Efficient Synthesis of Highly Functionalized Dihydropyrazoles from Alkynes, Hydrazines, and Aldehydes or Ketones
Yamato Suzuki, Saori Naoe, Shinya Oishi, Nobutaka Fujii, and Hiroaki OhnoOrganic Letters2012 14 (1), 326-329Polysubstituted dihydropyrazoles were directly obtained by a gold-catalyzed three-component annulation. This reaction consists of a Mannich-type coupling of alkynes with N,N′-disubstituted hydrazines and aldehydes/ketones followed by intramolecular ...
One-Pot Synthesis of Indole-Fused Scaffolds via Gold-Catalyzed Tandem Annulation Reactions of 1,2-Bis(alkynyl)-2-en-1-ones with Indoles
Xin Xie, Xiangwei Du, Yifeng Chen, and Yuanhong LiuThe Journal of Organic Chemistry2011 76 (21), 9175-9181One-Pot Synthesis of Indole-Fused Scaffolds via Gold-Catalyzed Tandem Annulation Reactions of 1,2-Bis(alkynyl)-2-en-1-ones with Indoles
Xin Xie, Xiangwei Du, Yifeng Chen, and Yuanhong LiuThe Journal of Organic Chemistry2011 76 (21), 9175-9181The gold-catalyzed tandem cyclization of 1,2-bis(alkynyl)-2-en-1-ones with indoles offers an efficient and straightforward route to indole-fused polycyclic systems. The process is realized through a cascade carbonyl-yne cyclization/Friedel–Crafts/indole-...
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History
- Published In Issue October 11, 2007
- Received August 3, 2007
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