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A Tandem Approach to Isoquinolines from 2-Azido-3-arylacrylates and α-Diazocarbonyl Compounds
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Abstract
2-Azido-3-arylacrylates react with α-diazocarbonyl compounds and triphenylphosphine to furnish isoquinolines in 60−92% yields. The tandem process involves a Wolff rearrangement, an aza-Wittig reaction, and an electrocyclic ring closure. The procedure is efficient, rapid, and general, and the substrates are readily available.
Citing Articles
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This article has been cited by 12 ACS Journal articles (5 most recent appear below).
Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen WangOrganic Letters2011 13 (24), 6362-6365Catalyst-Free Preparation of 1,2,4,5-Tetrasubstituted Imidazoles from a Novel Unexpected Domino Reaction of 2-Azido Acrylates and Nitrones
Bao Hu, Zhao Wang, Ning Ai, Jie Zheng, Xing-Hai Liu, Shang Shan, and Zhongwen WangOrganic Letters2011 13 (24), 6362-6365A highly efficient and convenient method for the synthesis of 1,2,4,5-tetrasubstituted imidazoles from readily accessible 2-azido acrylates and nitrones has been developed. This reaction proceeded under mild conditions without the assistance of any metal, ...
One-Pot Synthesis of Pyrrolo[3,2-d]pyridazines and Pyrrole-2,3-diones via Zirconocene-Mediated Four-Component Coupling of Si-Tethered Diyne, Nitriles, and Azide
Shaoguang Zhang, Jing Zhao, Wen-Xiong Zhang, and Zhenfeng XiOrganic Letters2011 13 (7), 1626-1629One-Pot Synthesis of Pyrrolo[3,2-d]pyridazines and Pyrrole-2,3-diones via Zirconocene-Mediated Four-Component Coupling of Si-Tethered Diyne, Nitriles, and Azide
Shaoguang Zhang, Jing Zhao, Wen-Xiong Zhang, and Zhenfeng XiOrganic Letters2011 13 (7), 1626-1629A one-pot synthesis of pyrrolo[3,2-d]pyridazine derivatives via zirconocene-mediated four-component coupling of one Si-tethered diyne, two nitriles, and one azide is reported. When TMSN3 was used, pyrrole-2,3-diones were formed in good yields. Further ...
Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Copper(II)-Catalyzed Oxidation of an Aliphatic C−H Bond of Tertiary Amine in Air
Shaoyu Li and Jie WuOrganic Letters2011 13 (4), 712-715Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Copper(II)-Catalyzed Oxidation of an Aliphatic C−H Bond of Tertiary Amine in Air
Shaoyu Li and Jie WuOrganic Letters2011 13 (4), 712-715A multicomponent reaction of 2-alkynylbenzaldehyde, sulfonohydrazide, and tertiary amine is discovered, which generates the unexpected H-pyrazolo[5,1-a]isoquinolines in good yields under mild conditions. In the reaction process, silver(I)-catalyzed ...
Synthesis of 2-Azaanthracenes via a Sequential Sonogashira Coupling/Alkynyl Imine−Allenyl Imine Isomerization/Aza-Diels−Alder/Elimination−Aromatization Reaction
Jian Cao, Xiongfa Yang, Xilin Hua, Yuan Deng, and Guoqiao LaiOrganic Letters2011 13 (3), 478-481Synthesis of 2-Azaanthracenes via a Sequential Sonogashira Coupling/Alkynyl Imine−Allenyl Imine Isomerization/Aza-Diels−Alder/Elimination−Aromatization Reaction
Jian Cao, Xiongfa Yang, Xilin Hua, Yuan Deng, and Guoqiao LaiOrganic Letters2011 13 (3), 478-481An interesting sequential Sonogashira coupling/alkynyl imine−allenyl imine isomerization/aza-Diels−Alder/elimination−aromatization reaction, providing a facile synthesis of substituted 2-azaanthracenes from 1,6-diynes and imidoyl chlorides, is reported. ...
Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates
Deng Hong, Zhengbo Chen, Xufeng Lin, and Yanguang WangOrganic Letters2010 12 (20), 4608-4611Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates
Deng Hong, Zhengbo Chen, Xufeng Lin, and Yanguang WangOrganic Letters2010 12 (20), 4608-46112-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. ...
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History
- Published In Issue May 16, 2008
- Article ASAPApril 10, 2008
- Received: February 7, 2008
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