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Synthesis of optically active trifluoromethyl-substituted 2,3-dihydroimidazo[2,1-b]oxazoles


Mlostoń, Grzegorz; Wroblewska, Aneta; Heimgartner, Heinz (2016). Synthesis of optically active trifluoromethyl-substituted 2,3-dihydroimidazo[2,1-b]oxazoles. Journal of Fluorine Chemistry, 189:1-6.

Abstract

The 2-unsubstituted imidazole N-oxides with a 3,3,3-trifluoro-2-hydroxypropyl group at N(1) in the presence of acetic anhydride undergo cyclization via the intramolecular nucleophilic attack of the hydroxyl group onto C(2) of the imidazole ring to give trifluoromethylated derivatives of 2,3-dihydroimidazo[2,1-b]oxazoles. This method, starting with enantiopure substrates, allows the preparation of enantiopure products in a one-pot procedure.

Abstract

The 2-unsubstituted imidazole N-oxides with a 3,3,3-trifluoro-2-hydroxypropyl group at N(1) in the presence of acetic anhydride undergo cyclization via the intramolecular nucleophilic attack of the hydroxyl group onto C(2) of the imidazole ring to give trifluoromethylated derivatives of 2,3-dihydroimidazo[2,1-b]oxazoles. This method, starting with enantiopure substrates, allows the preparation of enantiopure products in a one-pot procedure.

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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
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Environmental Chemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Language:English
Date:July 2016
Deposited On:05 Aug 2016 09:18
Last Modified:30 Jul 2020 22:14
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center (Cracow) (Grants: OPUS-7 # UMO-2014/13/B/ST5/04004, and PRELUDIUM # UMO-2012/07/N/ST5/01873).
OA Status:Green
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2016.07.014

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