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

Journal article

Peer reviewed

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

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

Synthesis (Stuttgart), Vol.2007(22), pp.3473-3488

16/11/2007

DOI: https://doi.org/10.1055/s-2007-990856

Abstract

paper

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 HCO 2 NH 4 .

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Title: C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation
Creators - without role: Yun Zhi Zhang - 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
Kaïss Aouadi - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Guo-Rong Chen - 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
Jean-Pierre Praly - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Publication Details: Synthesis (Stuttgart), Vol.2007(22), pp.3473-3488
Identifiers: 9928532908331
Academic Unit: Qassim University
Language: English
Resource Type: Journal article