New -amino--trifluoromethyl alcohols and their exploration in the synthesis of trifluoromethylated imidazole derivatives

Racemic and enantiomerically pure �-amino-�-trifluoromethyl alcohols were obtained via sequential nucleophilic trifluoromethylation of selected �-imino ketones, derived from arylglyoxals, and subsequent removal of the MeO or Ph(Me)CH substituent, respectively, located at the N-atom. The obtained products, containing a primary amino group, were used for the synthesis of imidazole N-oxides bearing a trifluoromethyl group as a part of the N(1)-alkyl chain. Imidazole N-oxides with an electronwithdrawing ester group at C(4) underwent spontaneous isomerization under the reaction conditions, and the corresponding imidazol-2-one derivatives were isolated as final products. DOI: https://doi.org/10.1016/j.jfluchem.2011.07.016 Posted at the Zurich Open Repository and Archive, University of Zurich ZORA URL: https://doi.org/10.5167/uzh-49933 Accepted Version Originally published at: Mloston, G; Obijalska, E; Heimgartner, H (2011). New �-amino-�-trifluoromethyl alcohols and their exploration in the synthesis of trifluoromethylated imidazole derivatives. Journal of Fluorine Chemistry, 132(11):951-955. DOI: https://doi.org/10.1016/j.jfluchem.2011.07.016 New β-amino-α-trifluoromethyl alcohols and their exploration in the synthesis of trifluoromethylated imidazole derivatives Grzegorz Mlostoń, Emilia Obijalska and Heinz Heimgartner Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, PL-91403, Łódź, Poland Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH8057 Zurich, Switzerland