Document Detail


Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations.
MedLine Citation:
PMID:  15932305     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolin-2(1H)-ones can be conveniently prepared by treatment of alpha-halocarboxylic acid esters of salicylaldehyde, o-hydroxyacetophenone, methyl salicylate, and methyl N-methyl- or N-phenylanthranilates with sodium or lithium telluride. Phenylketene formation competes with cyclization of the alpha-chlorophenylacetate ester of methyl salicylate as demonstrated by a trapping experiment with benzylamine. Elemental tellurium may be recovered and reused.
Authors:
Donald C Dittmer; Qun Li; Dimitry V Avilov
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  70     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2005 Jun 
Date Detail:
Created Date:  2005-06-03     Completed Date:  2005-07-13     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4682-6     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Syracuse University, Room 1-014 CST, Syracuse, New York 13244, USA. dcdittme@syr.edu
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Coumarins / chemical synthesis*
Cyclization
Hydroxyquinolines / chemical synthesis*
Indicators and Reagents
Molecular Structure
Tellurium / chemistry*
Chemical
Reg. No./Substance:
0/Coumarins; 0/Hydroxyquinolines; 0/Indicators and Reagents; 13494-80-9/Tellurium

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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