Efficient one-pot synthesis of deoxyfructosazine and fructosazine from D-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst

Lingyu Jia; Yingxiong Wang; Yan Qiao; Yongqin Qi; Xianglin Hou

doi:10.1039/C4RA06832G

Efficient one-pot synthesis of deoxyfructosazine and fructosazine from D-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst

Lingyu Jia,^a^b Yingxiong Wang,^a Yan Qiao,^a Yongqin Qi^a and Xianglin Hou*^a

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* Corresponding authors

^a State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, 27 South Taoyuan Road, Taiyuan, PR China
E-mail: houxl@sxicc.ac.cn
Fax: +86 351 4041153
Tel: +86 351 4049501

^b University of Chinese Academy of Sciences, Beijing, PR China

Abstract

An efficient one-pot dehydration process for convert D-glucosamine hydrochloride (GlcNH₂) into 2-(D-arabino-1′,2′,3′,4′-tetrahydroxybutyl)-5-(D-erythro-2′′,3′′,4′′-trihydroxybutyl)pyrazine (deoxyfructosazine, DOF) and 2,5-bis-(D-arabino-1,2,3,4-tetrahydroxybutyl)pyrazine (fructosazine, FZ) was reported. A task-specific basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), was employed as an environmentally-friendly solvent and catalyst. The products were qualitatively and quantitatively characterized by MALDI-TOF-MS, ¹H NMR and ¹³C NMR spectroscopy. The influences of GlcNH₂ concentrations, reaction temperature, reaction time, additives and co-solvents on the yields of products were studied. The maximum yield of 49% was obtained in the presence of [BMIM]OH and DMSO under optimized conditions (120 °C, 180 min). In addition, a plausible mechanism was proposed. Our project was to develop efficient, atom economical and eco-compatible routes for the synthesis of heterocyclic compounds from marine biomass (or nitrogen-containing biomass). The obtained aromatic heterocyclic compounds showed potential pharmacological action and physiological effects, and they also could be utilized as flavoring agents in the food industry.

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Publication details

The article was received on 09 Jul 2014, accepted on 04 Sep 2014 and first published on 09 Sep 2014

Article type: Paper

DOI: 10.1039/C4RA06832G

Citation: RSC Adv., 2014,4, 44253-44260

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Efficient one-pot synthesis of deoxyfructosazine and fructosazine from D-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst

L. Jia, Y. Wang, Y. Qiao, Y. Qi and X. Hou, RSC Adv., 2014, 4, 44253
DOI: 10.1039/C4RA06832G
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Efficient one-pot synthesis of deoxyfructosazine and fructosazine from D-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst

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Efficient one-pot synthesis of deoxyfructosazine and fructosazine from D-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst

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