Document Detail


New polycyclic diamine scaffolds from dimerization of 3-alkyl-1,4-dihydropyridines in acidic medium.
MedLine Citation:
PMID:  16149815     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
[reaction: see text] 3-Alkyl-1,4-dihydropyridines dimerize in acidic medium, at low temperature, to give polycyclic imminium salts derivatives that were reduced to afford new polycyclic diamine scaffolds. The reaction can be extended to enantiopure series starting from R-(+)- or S-(-)-1-phenylethylamine. Long exposure of the polycyclic imminium salt intermediates to air moisture at 20 degrees C resulted in formation of new amide derivatives. This is probably due to the addition of water followed by an intramolecular oxido-reduction process.
Authors:
Karine Jakubowicz; Yung-Sing Wong; Angèle Chiaroni; Michel Bénéchie; Christian Marazano
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  70     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2005 Sep 
Date Detail:
Created Date:  2005-09-09     Completed Date:  2006-04-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7780-3     Citation Subset:  -    
Affiliation:
Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
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Erratum In:
J Org Chem. 2006 Feb 3;71(3):1288

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