Document Detail


Enaminones in heterocyclic synthesis: a novel route to tetrahydropyrimidines, dihydropyridines, triacylbenzenes and naphthofurans under microwave irradiation.
MedLine Citation:
PMID:  20110871     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Condensation of phthalimidoacetone (1) with DMFDMA (N,N-Dimethylformamide dimethyl acetal) has afforded enaminone 2. Refluxing 2 with equimolecular amounts of benzaldehyde and urea in acetic acid afforded a mixture of tetrahydropyrimidine 5 and the dihydropyridine 6. Compound 2 undergoes self-condensation on heating in acetic acid or under microwave irradiation in presence of acidic zeolite to give 1,3,5-triacylbenzene 9. Reacting enaminone 11a with naphthoquinone 15 afforded the naphthofuran 18. The possible formation of the aldehyde 19 was excluded based on an HMQC experiment, which revealed that the carbonyl carbon is not linked to any hydrogen.
Authors:
Saleh Mohammed Al-Mousawi; Morsy Ahmed El-Apasery; Mohamed H Elnagdi
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-12-25
Journal Detail:
Title:  Molecules (Basel, Switzerland)     Volume:  15     ISSN:  1420-3049     ISO Abbreviation:  Molecules     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2010-01-29     Completed Date:  2010-04-02     Revised Date:  2010-12-15    
Medline Journal Info:
Nlm Unique ID:  100964009     Medline TA:  Molecules     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  58-67     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Faculty of Science; Kuwait University, P.O. Box 5969 Safat 13060, Kuwait. saleh.almousawi@yahoo.com
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MeSH Terms
Descriptor/Qualifier:
Benzene / chemical synthesis*,  chemistry
Dihydropyridines / chemical synthesis*,  chemistry
Furans / chemical synthesis*,  chemistry
Heterocyclic Compounds, 2-Ring / chemical synthesis*,  chemistry
Microwaves*
Pyrimidines / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Dihydropyridines; 0/Furans; 0/Heterocyclic Compounds, 2-Ring; 0/Pyrimidines; 71-43-2/Benzene

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