Palladium(0)-catalyzed efficient synthesis of allylic N- and S-benzoheterocycles linked to unsaturated carbohydrate derivatives

<div>An efficient strategy was developed to envisage the synthesis of new N- and S-benzoheterocycles attached to the C-4 position of pseudo-carbohydrates. The reaction was performed with unsaturated carbohydrates and benzoheterocycles as nucleophiles in the presence of a catalytic amo...

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Bibliographic Details
Main Authors: Ronaldo Nascimento de Oliveira, Wilson S. do Nascimento, Girliane R. da Silva, Tânia Maria S. Silva
Format: Article
Language:English
Published: Universidade Federal de Mato Grosso do Sul 2012-07-01
Series:Orbital: The Electronic Journal of Chemistry
Subjects:
Online Access:http://orbital.ufms.br/index.php/Chemistry/article/view/310
Description
Summary:<div>An efficient strategy was developed to envisage the synthesis of new N- and S-benzoheterocycles attached to the C-4 position of pseudo-carbohydrates. The reaction was performed with unsaturated carbohydrates and benzoheterocycles as nucleophiles in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) and chelating bidentate ligand dppb. This strategy allowed easy access to benzoheterocyclic sugars in moderate-to-good yields. A preliminary study for antioxidant activities of O-glycosides 2,3-unsaturated was evaluated based on the 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging and 2,2-azinobis 3-ethylbenzothiozoline-6-sulfonic acid (ABTS) radical cation decolorization assay, and showed low-to-moderate activities.</div>
ISSN:1984-6428