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Assembly of Isoquinolines via CuI-Catalyzed Coupling of β-Keto Esters and 2-Halobenzylamines
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China Pharmaceutical University.
, ‡Chinese Academy of Sciences.
Abstract
CuI-catalyzed coupling of 2-halobenzylamines with β-keto esters or 1,3-diketones in i-PrOH under the action of K2CO3 produced 1,2-dihydroisoquinolines as the coupling/condensative cyclization products, which underwent smooth dehydrogenation under air atmosphere to afford substituted isoquinolines.
Citing Articles
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This article has been cited by 22 ACS Journal articles (5 most recent appear below).
The N-Aryl Aminocarbonyl ortho-Substituent Effect in Cu-Catalyzed Aryl Amination and Its Application in the Synthesis of 5-Substituted 11-Oxo-dibenzodiazepines
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Xiaoqiong Diao, Lanting Xu, Wei Zhu, Yongwen Jiang, Haoyang Wang, Yinlong Guo, and Dawei MaOrganic Letters2011 13 (24), 6422-6425Double amination of ortho-substituted aryl bromides proceeded under mild conditions to afford 5-substituted 11-oxo-dibenzodiazepines, which revealed that there is a strong ortho-substituent effect caused by N-aryl aminocarbonyl groups during copper-...
Amino Acids as the Nitrogen-Containing Motifs in Copper-Catalyzed Domino Synthesis of N-Heterocycles
Wei Xu and Hua FuThe Journal of Organic Chemistry2011 76 (10), 3846-3852Amino Acids as the Nitrogen-Containing Motifs in Copper-Catalyzed Domino Synthesis of N-Heterocycles
Wei Xu and Hua FuThe Journal of Organic Chemistry2011 76 (10), 3846-3852A copper-catalyzed domino method for synthesis of quinazolinones has been developed using readily available α-amino acids as the nitrogen-containing motifs. The domino process underwent Ullmann-type N-arylation, decarboxylation, aerobic oxidation, and ...
Copper-Catalyzed Cascade Synthesis of Alkyl 6-Aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates
Juyou Lu and Hua FuThe Journal of Organic Chemistry2011 Article ASAPCopper-Catalyzed Cascade Synthesis of Alkyl 6-Aminobenzimidazo[2,1-a]isoquinoline-5-carboxylates
Juyou Lu and Hua FuThe Journal of Organic Chemistry2011 Article ASAPA convenient and efficient copper-catalyzed cascade method has been developed for synthesis of benzimidazoisoquinoline derivatives via reactions of readily available substituted 2-(2-halophenyl)benzoimidazoles with alkyl cyanoacetates under mild condition,...
Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of 4H-Chromenes and Naphthalenes
Chandi C. Malakar, Dietmar Schmidt, Jürgen Conrad, and Uwe BeifussOrganic Letters2011 13 (8), 1972-1975Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of 4H-Chromenes and Naphthalenes
Chandi C. Malakar, Dietmar Schmidt, Jürgen Conrad, and Uwe BeifussOrganic Letters2011 13 (8), 1972-1975Depending on the ratio of the substrates and the reaction conditions, the Cu(I)-catalyzed domino reaction between bromobenzyl bromides and β-ketoesters exclusively yields either 4H-chromenes or naphthalenes.
Copper-Catalyzed Domino Synthesis of Quinazolinones via Ullmann-Type Coupling and Aerobic Oxidative C−H Amidation
Wei Xu, Yibao Jin, Hongxia Liu, Yuyang Jiang, and and Hua FuOrganic Letters2011 13 (6), 1274-1277Copper-Catalyzed Domino Synthesis of Quinazolinones via Ullmann-Type Coupling and Aerobic Oxidative C−H Amidation
Wei Xu, Yibao Jin, Hongxia Liu, Yuyang Jiang, and and Hua FuOrganic Letters2011 13 (6), 1274-1277An efficient copper-catalyzed approach to quinazolinone derivatives has been developed, and the protocol uses cheap and readily available substituted 2-halobenzamides and (aryl)methanamines as the starting materials as well as economical and ...
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History
- Published In Issue July 03, 2008
- Article ASAPMay 29, 2008
- Received: April 18, 2008
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