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One-Pot Selective Syntheses of 5-Azaindoles through Zirconocene-Mediated Multicomponent Reactions with Three Different Nitrile Components and One Alkyne Component
Zhang, Shaoguang1; Zhang, Wen-Xiong1; Zhao, Jing2; Xi, Zhenfeng1,3
2011-02-01
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
ISSN0947-6539
Volume17Issue:8Pages:2442-2449
Abstract5-Azaindoles either with three different substituents at their 2-, 4-, and 6-positions or with two identical substituents at their 2- and 6-positions and a different one at the 4-position, were obtained in good to excellent isolated yields by a zirconocene-mediated multicomponent process. Each reaction involved four organic partners, comprising a Si-tethered diyne, one tBuCN component, and two (either different or identical) nitriles. All these four components were combined through the action of a Cp2ZrII species into a three-ring fused Zr/Si-containing organometallic complex in a perfectly chemo-and regioselective manner. This multicomponent reaction process consisted of three reaction steps, all of which were made clear through the isolation and characterization of their cor-responding organometallic intermediates: the zirconacyclopropene-azasila-cyclopentadienes 2, the allenyl-aza-zirconacycles 3, and the three-ring fused complexes 6. X-ray single-crystal structural analyses of two three-ring fused Zr/Si-containing intermediates and two 5-azaindoles unambiguously showed the positions of the different substituents and the regioselectivity. Iminopyrrole derivatives could be also highly selectively prepared from a Si-tethered diyne and two different nitriles.
Keyword5-azaindoles Multicomponent Reactions Nitriles Nitrogen Heterocycles Zirconium
DOI10.1002/chem.201003119
Indexed BySCI ; IC
Language英语
WOS IDWOS:000288096800021
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Cited Times:23[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/71746
Collection中国科学院化学研究所
Corresponding AuthorXi, Zhenfeng
Affiliation1.Peking Univ, Coll Chem, Minist Educ,Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
2.CAS, Inst Chem, Beijing 100190, Peoples R China
3.Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
Recommended Citation
GB/T 7714
Zhang, Shaoguang,Zhang, Wen-Xiong,Zhao, Jing,et al. One-Pot Selective Syntheses of 5-Azaindoles through Zirconocene-Mediated Multicomponent Reactions with Three Different Nitrile Components and One Alkyne Component[J]. CHEMISTRY-A EUROPEAN JOURNAL,2011,17(8):2442-2449.
APA Zhang, Shaoguang,Zhang, Wen-Xiong,Zhao, Jing,&Xi, Zhenfeng.(2011).One-Pot Selective Syntheses of 5-Azaindoles through Zirconocene-Mediated Multicomponent Reactions with Three Different Nitrile Components and One Alkyne Component.CHEMISTRY-A EUROPEAN JOURNAL,17(8),2442-2449.
MLA Zhang, Shaoguang,et al."One-Pot Selective Syntheses of 5-Azaindoles through Zirconocene-Mediated Multicomponent Reactions with Three Different Nitrile Components and One Alkyne Component".CHEMISTRY-A EUROPEAN JOURNAL 17.8(2011):2442-2449.
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