New 1-alkyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazolium bromides
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STYNGACH, Evgenia, BARBA, Alic, MAKAEV, Fliur. New 1-alkyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazolium bromides. In: The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova, 28-30 mai 2014, Chișinău. Chișinău, Republica Moldova: Institutul de Chimie al AȘM, 2014, p. 215.
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The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova 2014
Conferința "The International Conference dedicated to the 55th anniversary from the foundation of the Institute of Chemistry of the Academy of Sciences of Moldova"
Chișinău, Moldova, 28-30 mai 2014

New 1-alkyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imidazolium bromides


Pag. 215-215

Styngach Evgenia, Barba Alic, Makaev Fliur
 
Institute of Chemistry of the Academy of Sciences of Moldova
 
Disponibil în IBN: 23 iunie 2020


Rezumat

Glucopyranoside-incorporated imidazolium bromides can exhibit interesting ionic liquid
properties, and the recent work on these compounds has been dedicated to the search for
effective N-heterocyclic carbene (NHC) precursor [1]. Synthesis of ionic liquids generally
involves construction of the organic base from an appropriate amino compound, which in the
case of 1H-imidazole 1a is compound 1b-1d [2-4].
As part of a research program to examine the effect of the structural features of the N-alkyl
moiety of imidazoles 1b, 1c, 1d on the properties of glucopyranoside-incorporated imidazolim
bromides 3a-3c, we required 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 2.
Herein, we describe a successful synthetic approach to 3a starting from readily available Nmethylimidazole
1b and bromide 2 (see the scheme bellow).

This approach should be equally applicable to synthesis of 3b from imidazole 1c (also
available commercially). 3-(1H-imidazol-1-yl)propanenitrile 1d and 2,3,4,6-tetra-O-acetyl-α-Dglucopyranosyl
bromide 2 are also useful for construction chiral ionic liquid 3c.
We thank the bilateral MD-UC project (Ref. № 14.820.18.02.06/U) for financial support.
References:
1. Nishioka T., Shibata T., Kinoshita I. Organometallics 2007, 26, 1126.
2. Macaev F., Styngach E., Shargarovskii V., Bets L., Vlad L., Barba A. Russ. J. Org. Chem.
2010, 46 (4), 610.