jo961723x_si_001.pdf (1.05 MB)
An Unusual Trifluoromethyl Elimination Reaction from the 4,4-Bis(trifluoromethyl)-5-hydroxyimidazoline Ring System
journal contribution
posted on 1997-04-18, 00:00 authored by Hui-Yin Li, Indawati DeLucca, Spencer Drummond, George A. BoswellA facile detrifluoromethylation was observed when
4,4-bis(trifluoromethyl)-5-hydroxyimidazoline
5 was treated with a variety of bases to afford the
biologically interesting 4-(trifluoromethyl)imidazole analogs (9 and 10). A unique
mechanism was proposed for this transformation, supported
by isolating and trapping the hypothesized intermediates. Heating
of 5 with Et4NCN in DMSO
provided 19, which was clearly derived from the proposed
intermediate 17. Finally, imidazole
9
was converted into the
N-[2-phenyl-4-(trifluoromethyl)-1H-imidazol-5-yl]-N-methylbenzamide
analogs, which were potential acyl CoA:cholesterol acyltransferase (ACAT)
inhibitors.