Title :

The Reactivity of Enantiopure (S)-6-Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions

Author(s) :

Šafář, Peter [Auteur]
Slovak University of Technology in Bratislava [STU]
Marchalín, Štefan [Auteur correspondant]
Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire [INC3M]
Slovak University of Technology in Bratislava [STU]
Unité de Recherche en Chimie Organique et Macromoléculaire [URCOM]
Balónová, Barbora [Auteur]
University of Kent [Canterbury]
Šoral, Michal [Auteur]
Slovak University of Technology in Bratislava [STU]
Moncol, Ján [Auteur]
Slovak University of Technology in Bratislava [STU]
Ghinet, Alina [Auteur]
Facteurs de Risque et Déterminants Moléculaires des Maladies liées au Vieillissement - U 1167 [RID-AGE]
Hautes Etudes d’Ingénieur [Lille] [HEI]
Alexandru Ioan Cuza University of Iași = Universitatea Alexandru Ioan Cuza din Iași [UAIC]
Lille Inflammation Research International Center - U 995 [LIRIC]
Rigo, Benoît [Auteur]
Hautes Etudes d’Ingénieur [Lille] [HEI]
Lille Inflammation Research International Center - U 995 [LIRIC]
Daïch, Adam [Auteur correspondant]
Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire [INC3M]
Slovak University of Technology in Bratislava [STU]
Unité de Recherche en Chimie Organique et Macromoléculaire [URCOM]

Journal title :

European Journal of Organic Chemistry

Pages :

5499-5511

Publisher :

Wiley-VCH Verlag

Publication date :

2018-10-18

ISSN :

1434-193X

English keyword(s) :

Nitrogen heterocycles
Polycycles
Amino acids
Cyclization
N-Acyliminium Species

HAL domain(s) :

Chimie

English abstract : [en]

Enantiopure N-benzyl 6-oxopipecolic acid, obtained from (S)-2-aminoadipic acid, was evaluated under π-cationic cyclization conditions. If the combination of SOCl2/AlCl3 seems to be superior in terms of the reaction yields, ...
Show more >Enantiopure N-benzyl 6-oxopipecolic acid, obtained from (S)-2-aminoadipic acid, was evaluated under π-cationic cyclization conditions. If the combination of SOCl2/AlCl3 seems to be superior in terms of the reaction yields, use of PPA, (CF3CO)2O/BF3·Et2O, and Eaton's reagent is also very interesting since in addition to the expected keto-lactam, reduced- and oxidized keto-lactam, enamides and enamidones containing CF3CO– residue are isolated. Mechanisms leading to these products as well as the ones resulting from their acidic treatment were proposed and discussed with the help, in some cases, of univocal transformations and X-ray analysis.Show less >

Language :

Anglais

Peer reviewed article :

Oui

Audience :

Internationale

Popular science :

Non

Collections :

• Facteurs de risque et déterminants moléculaires des maladies liées au vieillissement (RID-AGE) - U1167

Source :

Harvested from HAL