Document Detail


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.
25156719 - Recycling of electric arc furnace dust through dissolution in deep eutectic ionic liqui...
22614629 - Direct and facile synthesis of carbon substituted alkylhydroxy derivatives of cobalt bi...
23795099 - 4-(4-bromo-phen-yl)-2-methyl-amino-3-nitro-5,6,7,8-tetra-hydro-4h-chromen-5-one.
25168229 - Simultaneous spectrophotometric determination of fe(iii) and al(iii) using orthogonal s...
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...