Synthesis and Antimicrobial Activity of Imidazolium and Triazolium Chiral Ionic Liquids

被引：41

作者：

Borowiecki, Pawel ^{[1
]}

Milner-Krawczyk, Malgorzata ^{[1
]}

Brzezinska, Dominika ^{[1
]}

Wielechowska, Monika ^{[1
]}

Plenkiewicz, Jan ^{[1
]}

机构：

[1] Warsaw Univ Technol, Fac Chem, PL-00664 Warsaw, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 04期

关键词：

Ionic liquids; Chirality; Enzyme catalysis; Kinetic resolution; Antibiotics; Antifungal agents; TRANSFER RADICAL POLYMERIZATION; ASYMMETRIC MICHAEL ADDITION; DESIGN; ORGANOCATALYSTS; SOLVENTS; MEDIA;

D O I：

10.1002/ejoc.201201245

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 gramnegative and gram-positive bacteria and fungi.

引用

页码：712 / 720

页数：9

共 60 条

[1] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].

Baudequin, C ;

Brégeon, D ;

Levillain, J ;

Guillen, F ;

Plaquevent, JC ;

Gaumont, AC .

TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945

[2] Design and synthesis of novel ionic liquid/liquid crystals (IL 2Cs) with axial chirality [J].

Baudoux, J ;

Judeinstein, P ;

Cahard, D ;

Plaquevent, JC .

TETRAHEDRON LETTERS, 2005, 46 (07) :1137-1140

[3] Radical polymerization in a chiral ionic liquid: Atom transfer radical polymerization of acrylates [J].

Biedron, T ;

Kubisa, P .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2005, 43 (15) :3454-3459

[4] Ionic liquids as reaction media for polymerization processes: atom transfer radical polymerization (ATRP) of acrylates in ionic liquids [J].

Biedron, T ;

Kubisa, P .

POLYMER INTERNATIONAL, 2003, 52 (10) :1584-1588

[5]

Borowiecki P., 2010, THESIS WARSAW U TECH

[6] Preparation and thermal stability of optically active 1,2,4-triazolium-based ionic liquids [J].

Borowiecki, Pawel ;

Poterala, Marcin ;

Maurin, Jan ;

Wielechowska, Monika ;

Plenkiewicz, Jan .

ARKIVOC, 2012, :262-281

[7] Antibiofilm activities of 1-alkyl-3-methylimidazolium chloride ionic liquids [J].

Carson, Louise ;

Chau, Peter K. W. ;

Earle, Martyn J. ;

Gilea, Manuela A. ;

Gilmore, Brendan F. ;

Gorman, Sean P. ;

McCann, Maureen T. ;

Seddon, Kenneth R. .

GREEN CHEMISTRY, 2009, 11 (04) :492-497

[8] Design and synthesis of imidazolinium salts derived from (L)-valine. Investigation of their potential in chiral molecular recognition [J].

Clavier, H ;

Boulanger, L ;

Audic, N ;

Toupet, L ;

Mauduit, M ;

Guillemin, JC .

CHEMICAL COMMUNICATIONS, 2004, (10) :1224-1225

[9] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[10]

Denny W. A., 2004, [No title captured], Patent No. [US 2004/0044057 A1, 20040044057]

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