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Optically active imidazole N-oxides derived from L-prolinamine


Mloston, Grzegorz; Wroblewska, Aneta; Obijalska, Emilia; Heimgartner, Heinz (2013). Optically active imidazole N-oxides derived from L-prolinamine. Tetrahedron: Asymmetry, 24(15-16):958-965.

Abstract

Starting with (S)-1-benzylprolinamine and alpha-hydroxyimino ketones, enantiomerically pure bisheterocyclic imidazole N-oxides bearing the (S)-configured N-benzyl(pyrrolidin-2-yl)methyl residue were prepared. These N-oxides reacted with 2,2,4,4-tetramethylcyclobutane-1,3-dithione to give the corresponding optically active imidazole-2-thione derivatives via a sulfur transfer reaction. Reduction of the N-oxides with Raney-nickel led to deoxygenation, whereas catalytic hydrogenation (Pd/C) in ethanol occurred with simultaneous deoxygenation and debenzylation, leading to optically active 1-(pyrrolidin-2-yl)methyl-1H-imidazoles. Alkylation of the prepared imidazole N-oxides and their respective imidazoles with butyl and hexyl bromide and subsequent anion exchange gave optically active N-alkoxy- and N-alkyl-imidazolium tetrafluoroborates, respectively, with the properties of ‘room temperature ionic liquids’.

Starting with (S)-1-benzylprolinamine and alpha-hydroxyimino ketones, enantiomerically pure bisheterocyclic imidazole N-oxides bearing the (S)-configured N-benzyl(pyrrolidin-2-yl)methyl residue were prepared. These N-oxides reacted with 2,2,4,4-tetramethylcyclobutane-1,3-dithione to give the corresponding optically active imidazole-2-thione derivatives via a sulfur transfer reaction. Reduction of the N-oxides with Raney-nickel led to deoxygenation, whereas catalytic hydrogenation (Pd/C) in ethanol occurred with simultaneous deoxygenation and debenzylation, leading to optically active 1-(pyrrolidin-2-yl)methyl-1H-imidazoles. Alkylation of the prepared imidazole N-oxides and their respective imidazoles with butyl and hexyl bromide and subsequent anion exchange gave optically active N-alkoxy- and N-alkyl-imidazolium tetrafluoroborates, respectively, with the properties of ‘room temperature ionic liquids’.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2013
Deposited On:16 Sep 2013 07:07
Last Modified:05 Apr 2016 16:58
Publisher:Elsevier
ISSN:0957-4166
Funders:National Science Center, Cracow (Grant Preludium UMO-2012/07/N/ST5)
Publisher DOI:https://doi.org/10.1016/j.tetasy.2013.07.013
Permanent URL: https://doi.org/10.5167/uzh-80783

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