Document Detail

Synthesis and transformations of a pyrazole containing alpha, beta-didehydro-alpha-amino acid derivatives.
MedLine Citation:
PMID:  12707809     Owner:  NLM     Status:  MEDLINE    
2H-Pyran-2-ones 1 were transformed with various hydrazines into (E)- or (Z)-alpha, beta-didehydro-alpha-amino acid (DDAA) derivatives 4 (and 7) containing a highly substituted pyrazolyl moiety attached at the beta-position. With heterocyclic hydrazines, the products 4 were accompanied also by decarboxylated enamines E-6. In order to separate (E/Z)-mixtures of acids, they were transformed to the corresponding methyl esters 9 and 10 by the application of diazomethane. Catalytic hydrogenation under high pressures with Pd/C as a catalyst resulted in the formation of racemic alanine derivatives 11.
L Vranicar; F Pozgan; S Polanc; M Kocevar
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Amino acids     Volume:  24     ISSN:  0939-4451     ISO Abbreviation:  Amino Acids     Publication Date:  2003 Apr 
Date Detail:
Created Date:  2003-04-22     Completed Date:  2004-03-09     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9200312     Medline TA:  Amino Acids     Country:  Austria    
Other Details:
Languages:  eng     Pagination:  273-80     Citation Subset:  IM    
Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, SI-1000 Ljubljana, Slovenia.
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MeSH Terms
Amino Acids / chemical synthesis*,  chemistry
Models, Chemical
Molecular Structure
Pyrans / chemistry
Pyrazoles / chemistry*
Reg. No./Substance:
0/Amino Acids; 0/Pyrans; 0/Pyrazoles; 288-13-1/pyrazole

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