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

ABSTRACT: Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with ?- or ?-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 ?- or ?-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of ?- or ?-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods.

SUBMITTER: Redjdal W

PROVIDER: S-EPMC6017768 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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

Redjdal Wafa W Ibrahim Nada N Benmerad Belkacem B Alami Mouad M Messaoudi Samir S

Molecules (Basel, Switzerland) 20180226 3

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. ...[more]

PMID: 29495402

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