| Aryne [3 + 2] cycloaddition with N-sulfonylpyridinium imides and in situ generated N-sulfonylisoquinolinium imides: a potential route to pyrido[1,2-b]indazoles and indazolo[3,2-a]isoquinolines. | |
| | |
MedLine Citation:
|
PMID: 22278679 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
The aryne [3 + 2] cycloaddition process with pyridinium imides breaks the aromaticity of the pyridine ring. By equipping the imide nitrogen with a sulfonyl group, the intermediate readily eliminates a sulfinate anion to restore the aromaticity, leading to the formation of pyrido[1,2-b]indazoles. The scope and limitation of this reaction are discussed. As an extension of this chemistry, N-tosylisoquinolinium imides, generated in situ from N'-(2-alkynylbenzylidene)-tosylhydrazides via an AgOTf-catalyzed 6-endo-dig electrophilic cyclization, readily undergo aryne [3 + 2] cycloaddition to afford indazolo[3,2-a]-isoquinolines in the same pot, offering a highly efficient route to these potential anticancer agents. |
| | |
Authors:
|
Jingjing Zhao; Pan Li; Chunrui Wu; Hongli Chen; Wenying Ai; Renhong Sun; Hailong Ren; Richard C Larock; Feng Shi |
Related Documents
:
|
22904789 - 2-[1-(1-oxoindan-2-yl)eth-yl]indan-1-one. 11389639 - The importance of the ene reaction for the c(2)-c(6) cyclization of enyne-allenes. 22614629 - Direct and facile synthesis of carbon substituted alkylhydroxy derivatives of cobalt bi... 22382869 - Enhancement of the electrochemical capacitance of tio(2) nanotube arrays through contro... 15549819 - Palladium-catalyzed [2 + 2 + 2] cocyclotrimerization of benzynes with bicyclic alkenes:... 18848799 - Ultrasound-promoted synthesis of novel dispirocyclic frameworks from aza-claisen rearra... 21837069 - 3'-(3-hy-droxy-phen-yl)-4-methyl-spiro-[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5(1h,4h)... 17887739 - Should contemporary density functional theory methods be used to study the thermodynami... 23073469 - Green/green-yellow-emitting ksrgd(po(4))(2):ce(3+), tb(3+)/mn(2+) phosphors with high q... |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2012-1-25 |
Journal Detail:
|
Title: Organic & biomolecular chemistry Volume: - ISSN: 1477-0539 ISO Abbreviation: - Publication Date: 2012 Jan |
Date Detail:
|
Created Date: 2012-1-26 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
|
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng, Henan 475004, China PR. cwu@henu.edu.cn fshi@henu.edu.cn. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: An Efficient Framework for Constructing Generalized Locally-Induced Text Metrics.
Next Document: Liver progenitor cell markers correlate with liver damage and predict short-term mortality in patien...