Synthesis and Antimicrobial Activity of Imidazolium and Triazolium Chiral Ionic Liquids
Paweł Borowiecki , Małgorzata Milner-Krawczyk , Dominika Brzezińska , Monika Wielechowska , Jan Plenkiewicz
AbstractA 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.
|Journal series||European Journal of Organic Chemistry, ISSN 1434-193X, [1099-0690]|
|Publication size in sheets||0.5|
|Keywords in English||Ionic liquids, Chirality, Enzyme catalysis, Kinetic resolution, Antibiotics, Antifungal agents|
|Score|| = 35.0, 17-08-2020, ArticleFromJournal|
= 35.0, 17-08-2020, ArticleFromJournal
|Publication indicators||= 29; = 29; = 5.0; : 2013 = 0.834; : 2013 = 3.154 (2) - 2013=3.001 (5)|
|Citation count*||5 (2015-10-29)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.