Synthesis and Antimicrobial Activity of Imidazolium and Triazolium Chiral Ionic Liquids

Abstract

A simple and efficient procedure for the synthesis of new optically active imidazolium and triazolium ionic liquids in a three step reaction sequence is described. In the first step, the ring opening of 1,2‐butylene oxide by imidazole or 1,2,4‐triazole resulted in the formation of N‐2‐hydroxybutylimidazole and N‐2‐hydroxybutyl‐1,2,4‐triazole, respectively. In the second step, racemic mixtures of the secondary alcohols were resolved with good enantioselectivity by a lipase‐catalyzed transesterification with enol esters (vinyl acetate and 1‐acetoxy‐2‐methylcyclohexene). In the final step, the optically active intermediates were alkylated with several haloalkanes to yield optically active ionic liquids. The inhibitory activity of the synthesized ionic liquids was tested towards gram‐negative and gram‐positive bacteria and fungi.

Chemoenzymatic synthesis and biological evaluation of enantiomerically enriched 1-(β-hydroxypropyl)imidazolium- and triazolium-based ionic liquids

“…This approach consists of comparing the differences between 1 H NMR chemical shifts recorded for the diastereomeric esters prepared from the separated enantiomers of the alcohols (+)- 5a or (+)- 5b and ( R )- and ( S )-enantiomers of methoxyphenylacetic acid (MPA, Mosher reagent) (Scheme 2). The utility of this method applied to secondary alcohols possessing heterocyclic azole rings has been demonstrated by us previously [58]. …”

Larvicidal and residual activity of imidazolium salts againstAedes aegypti(Diptera: Culicidae)

“…Imidazolium salts (IS) are ionic derivatives of the neutral imidazole heterocycle . They are typically composed of an organic imidazolium cation and an organic or inorganic anion; IS with a melting point of ≤100 °C are classified as ionic liquids.…”

BIOnic Liquids: Imidazolium-based Ionic Liquids with Antimicrobial Activity

“…The groups of Borowiecki [7,8] and Yin [9] have focussed their studies on ionic liquids bearing a hydroxy group in the cation. Their results were unsatisfactory; the OH group seemed to have little effect on the antimicrobial activity and the influence of the alkyl chain length remained dominant.…”