Synlett 2016; 27(06): 934-940
DOI: 10.1055/s-0035-1561333
letter
© Georg Thieme Verlag Stuttgart · New York

Triflic Acid Catalyzed Intermolecular α-Amination of Pterolactams To Give 5-Arylaminopyrrolidinones via N-Acyliminium Species

Gina-Mirabela Dumitriu
a  Department of Organic Chemistry, Faculty of Chemistry, ‘Al. I. Cuza’ University of Iasi, B-dul Carol I, Nr. 11, Corp A, 700506, Iasi, Romania
,
Elena Bîcu
a  Department of Organic Chemistry, Faculty of Chemistry, ‘Al. I. Cuza’ University of Iasi, B-dul Carol I, Nr. 11, Corp A, 700506, Iasi, Romania
,
Ulku Eryuruk
b  Hautes Etudes d’Ingénieur (HEI), Groupe HEI-ISA-ISEN, UCLille, Laboratoire de Pharmacochimie, 13 rue de Toul, BP 41290, 59014 Lille Cedex, France   Email: alina.ghinet@hei.fr
,
Dalila Belei
a  Department of Organic Chemistry, Faculty of Chemistry, ‘Al. I. Cuza’ University of Iasi, B-dul Carol I, Nr. 11, Corp A, 700506, Iasi, Romania
,
Benoît Rigo
b  Hautes Etudes d’Ingénieur (HEI), Groupe HEI-ISA-ISEN, UCLille, Laboratoire de Pharmacochimie, 13 rue de Toul, BP 41290, 59014 Lille Cedex, France   Email: alina.ghinet@hei.fr
c  Univ. Lille, Inserm, CHU Lille, U995-LIRIC-Lille Inflammation Research International Center, 59000 Lille, France
,
Adam Daïch*
d  URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences & Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France   Email: adam.daich@univ-lehavre.fr
,
Alina Ghinet*
a  Department of Organic Chemistry, Faculty of Chemistry, ‘Al. I. Cuza’ University of Iasi, B-dul Carol I, Nr. 11, Corp A, 700506, Iasi, Romania
b  Hautes Etudes d’Ingénieur (HEI), Groupe HEI-ISA-ISEN, UCLille, Laboratoire de Pharmacochimie, 13 rue de Toul, BP 41290, 59014 Lille Cedex, France   Email: alina.ghinet@hei.fr
c  Univ. Lille, Inserm, CHU Lille, U995-LIRIC-Lille Inflammation Research International Center, 59000 Lille, France
› Author Affiliations
Further Information

Publication History

Received: 01 November 2015

Accepted after revision: 30 December 2015

Publication Date:
26 January 2016 (online)


Abstract

A mild and efficient α-aza-amidoalkylation for the synthesis of 5-arylaminopyrrolidinones is presented. The key step of this reaction is the intermolecular interception of an N-acyliminium species, generated under the acidic conditions, with nitrogen nucleophiles such as N-silylamines.

Supporting Information

 
  • References and Notes

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