C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

Yun Zhi Zhang; Kaïss Aouadi; Guo-Rong Chen; Jean-Pierre Praly

doi:10.1055/s-2007-990856

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Synthesis 2007(22): 3473-3488
DOI: 10.1055/s-2007-990856

PAPER

C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation

Yun Zhi Zhang^a,b, Kaïss Aouadi^a, Guo-Rong Chen^b, Jean-Pierre Praly*^a
^a Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS, UMR5246, Université Lyon 1, CPE Lyon, bâtiment 308, 43 boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France
Fax: +33(4)72448349; e-Mail: jean-pierre.praly@univ-lyon1.fr;
^b Laboratory of Advanced Materials, Institute of Fine Chemicals, East China University of Science and Technology (ECUST), 130 Meilong Road, POB 257, 200237 Shanghai, P. R. of China

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Publication History

Received 20 June 2007
Publication Date:
29 October 2007 (online)

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Abstract

Reaction of C-β-d-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(β-d-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO₂NH₄.

Key words

glycosides - electrophilic aromatic substitution - hydrogen transfer - reduction - amines - amides

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