Document Detail


Synthetic routes to pyrrolizine-1,5-dione derivatives by flash vacuum pyrolysis of amidomethylene derivatives of Meldrum's acid.
MedLine Citation:
PMID:  19907784     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Methoxymethylene Meldrum's acid 1 reacts with 5- and 6-membered lactams in refluxing acetonitrile to give the N-substituted products 9-15. If the reactions are continued for extended times, the Meldrum's acid derivatives decompose to provide enamidoesters e.g. 22-24. Flash vacuum pyrolysis of the 5-membered ring products 9-13 provides reasonable yields of the fused pyrrolones 31-35. The constitution of the products is supported by X-ray crystal structures of 10, 12, 19, 32 and 34.
Authors:
Hamish McNab; Mark Morrow; Simon Parsons; David A Shannon; Kirsti Withell
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Publication Detail:
Type:  Journal Article     Date:  2009-10-01
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  7     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2009 Dec 
Date Detail:
Created Date:  2009-11-12     Completed Date:  2010-02-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  4936-42     Citation Subset:  IM    
Affiliation:
School of Chemistry, The University of Edinburgh, West Mains Road, Edinburgh, UK EH9 3JJ. H.McNab@ed.ac.uk
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MeSH Terms
Descriptor/Qualifier:
Acetonitriles / chemistry
Crystallography, X-Ray
Dioxanes / chemistry*
Lactams / chemistry
Models, Molecular
Molecular Structure
Pyrroles / chemical synthesis*,  chemistry
Stereoisomerism
Vacuum
Chemical
Reg. No./Substance:
0/Acetonitriles; 0/Dioxanes; 0/Lactams; 0/Pyrroles; 2033-24-1/Meldrum's acid; 75-05-8/acetonitrile

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


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