| Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations. | |
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MedLine Citation:
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PMID: 15932305 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Donald C Dittmer; Qun Li; Dimitry V Avilov |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 70 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2005 Jun |
Date Detail:
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Created Date: 2005-06-03 Completed Date: 2005-07-13 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4682-6 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Syracuse University, Room 1-014 CST, Syracuse, New York 13244, USA. dcdittme@syr.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Coumarins / chemical synthesis* Cyclization Hydroxyquinolines / chemical synthesis* Indicators and Reagents Molecular Structure Tellurium / chemistry* |
| Chemical | |
Reg. No./Substance:
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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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