An Unusual Trifluoromethyl Elimination Reaction from the 4,4-Bis(trifluoromethyl)-5-hydroxyimidazoline Ring System.

doi:10.1021/JO961723X

Paper

An Unusual Trifluoromethyl Elimination Reaction from the 4,4-Bis(trifluoromethyl)-5-hydroxyimidazoline Ring System.

Published Apr 18, 1997 · Hui‐Yin Li, I. Delucca, S. Drummond

The Journal of organic chemistry

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13

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Abstract

A 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 Et(4)NCN 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.

Study Snapshot

This study demonstrates a facile detrifluoromethylation reaction from 4,4-bis(trifluoromethyl)-5-hydroxyimidazoline to produce biologically interesting 4-(trifluoromethyl)imidazole analogs, potentially serving as ACAT inhibitors.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

An Unusual Trifluoromethyl Elimination Reaction from the 4,4-Bis(trifluoromethyl)-5-hydroxyimidazoline Ring System.

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