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Molecules 2018, 23(3), 519; https://doi.org/10.3390/molecules23030519

Convergent Synthesis of N,S-bis Glycosylquinolin-2-ones via a Pd-G3-XantPhos Precatalyst Catalysis

1
Laboratoire de Physico-Chimie des Matériaux et Catalyse, Faculté des Sciences Exactes, Université de Bejaia, 0600 Bejaia, Algeria
2
BioCIS, Université Paris-Sud, CNRS, University Paris-Saclay, 92296 Châtenay-Malabry, France
*
Authors to whom correspondence should be addressed.
Received: 29 January 2018 / Revised: 8 February 2018 / Accepted: 10 February 2018 / Published: 26 February 2018
(This article belongs to the Special Issue Glycomimetics: Design, Synthesis and Therapeutic Applications)
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Abstract

Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with α- or β-3-iodo-N-glycosylquinolin-2-ones has been accomplished under mild and operationally simple reaction conditions through the use of a Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or β-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of α- or β-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods. View Full-Text
Keywords: thiosugars; Buchwald-Hartwig-Migita coupling; N-glycosylquinolin-2-ones; bis-N,S-glycosyl quinolin-2-ones thiosugars; Buchwald-Hartwig-Migita coupling; N-glycosylquinolin-2-ones; bis-N,S-glycosyl quinolin-2-ones
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Redjdal, W.; Ibrahim, N.; Benmerad, B.; Alami, M.; Messaoudi, S. Convergent Synthesis of N,S-bis Glycosylquinolin-2-ones via a Pd-G3-XantPhos Precatalyst Catalysis. Molecules 2018, 23, 519.

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