Document Detail

Synthesis, structure and stability of 4-aryl-4H-pyran-3,5-dicarboxylic acid esters
MedLine Citation:
PMID:  12227190     Owner:  NLM     Status:  MEDLINE    
Eight new 4-aryl-2,6-dimethyl-4H-pyrane-3,5-dicarboxylic acid esters 2 and a new 2-amino-2-nor derivative 7 are synthesized using known methods, whose limitations are shown. In contrast to the isoelectronic 4-aryl-1,4-dihydro-pyridines (DHP) 1 the compounds 2e, g possess a nearly planar heterocycle, as found by X-ray crystal structure analysis. The 4H-pyrane-3,5-dicarboxylic acid ester 2e with m-substitution exhibits s-cis/s-cis-conformation, while compound 2g with o-substitution of the aromatic ring represents s-cis/s-trans-conformation. The half-wave potentials (E1/2) show that 4H-pyranes are more stable than the DHP 1. The substitution of the 4-phenyl ring with an electron donating group decreases the potential considerably, whereas an electron acceptor group slightly increases the potential. Replacement of the 2-methyl group by the amino function causes a dramatic loss of stability.
K Görlitzer; J Trittmacher; P G Jones
Publication Detail:
Type:  English Abstract; Journal Article    
Journal Detail:
Title:  Die Pharmazie     Volume:  57     ISSN:  0031-7144     ISO Abbreviation:  Pharmazie     Publication Date:  2002 Aug 
Date Detail:
Created Date:  2002-09-13     Completed Date:  2002-10-08     Revised Date:  2007-01-29    
Medline Journal Info:
Nlm Unique ID:  9800766     Medline TA:  Pharmazie     Country:  Germany    
Other Details:
Languages:  ger     Pagination:  523-9     Citation Subset:  IM    
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig, Germany.
Vernacular Title:
Darstellung, Struktur und Stabilität von 4-Aryl-4H-pyran-3,5-dicarbonsäureestern.
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MeSH Terms
Crystallography, X-Ray
Esters / chemical synthesis*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Models, Molecular
Pyrans / chemical synthesis*
Reg. No./Substance:
0/Esters; 0/Indicators and Reagents; 0/Pyrans

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