The Reactivity of Enantiopure (S)-6-Oxopipecolic ...
Type de document :
Article dans une revue scientifique: Article original
DOI :
URL permanente :
Titre :
The Reactivity of Enantiopure (S)-6-Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions
Auteur(s) :
Safar, Peter [Auteur]
Marchalin, Stefan [Auteur]
Balonova, Barbora [Auteur]
Soral, Michal [Auteur]
Moncol, Jan [Auteur]
Ghinet, Alina [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Rigo, Benoit [Auteur]
Daich, Adam [Auteur]
Marchalin, Stefan [Auteur]
Balonova, Barbora [Auteur]
Soral, Michal [Auteur]
Moncol, Jan [Auteur]
Ghinet, Alina [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Rigo, Benoit [Auteur]
Daich, Adam [Auteur]
Titre de la revue :
European Journal of Organic Chemistry
Nom court de la revue :
Eur. J. Org. Chem.
Numéro :
2018
Pagination :
5499-5511
Date de publication :
2018-11-01
ISSN :
1434-193X
Mot(s)-clé(s) en anglais :
Cyclization
Amino acids
N-Acyliminium Species
Nitrogen heterocycles
Polycycles
Amino acids
N-Acyliminium Species
Nitrogen heterocycles
Polycycles
Discipline(s) HAL :
Sciences du Vivant [q-bio]
Résumé en anglais : [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, ...
Lire la suite >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.Lire moins >
Lire la suite >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.Lire moins >
Langue :
Anglais
Audience :
Internationale
Vulgarisation :
Non
Établissement(s) :
CHU Lille
Inserm
Université de Lille
Inserm
Université de Lille
Équipe(s) de recherche :
Therapeutic innovation targetting inflammation
Date de dépôt :
2019-10-22T08:10:02Z
2023-12-08T10:30:36Z
2023-12-08T10:30:36Z