Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars

Boris Letribot; Wafa Redjdal; Belkacem Benmerad; Franck Le Bideau; Mouâd Alami; Samir Messaoudi

doi:10.1021/acs.orglett.0c01262

Synthesis of N-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars

Org Lett. 2020 Jun 5;22(11):4201-4206. doi: 10.1021/acs.orglett.0c01262. Epub 2020 May 13.

Authors

Boris Letribot¹, Wafa Redjdal^{1

2}, Belkacem Benmerad², Franck Le Bideau¹, Mouâd Alami¹, Samir Messaoudi¹

Affiliations

¹ Université Paris-Saclay, CNRS, BioCIS, 92290 Châtenay-Malabry, France.
² Laboratoire de Physico-Chimie des Matériaux et Catalyse, Faculté des Sciences Exactes, Université de Bejaia, 06000 Be-jaia, Algeria.

PMID: 32401034
DOI: 10.1021/acs.orglett.0c01262

Abstract

An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)₂/RuPhos catalytic systems in the presence of K₂CO₃. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Molecular Structure
Oxindoles / chemical synthesis*
Oxindoles / chemistry
Palladium / chemistry*
Sugars / chemistry*

Substances

Oxindoles
Sugars
2-oxindole
Palladium