AN UNUSUAL TRIFLUOROMETHYL ELIMINATION-REACTION FROM THE 4,4-BIS(TRIFLUOROMETHYL)-5-HYDROXYIMIDAZOLINE RING-SYSTEM

A facile detrifluoromethylation was observed when 4,4-bis(trifluoromet hyl)-5-hydroxyimidazoline 5 was treated with a variety of bases to aff ord the biologically interesting 4-(trifluoromethyl)imidazole analogs (9 and 10). A unique mechanism was proposed for this transformation, s upported by isolating and trapping the hypothesized intermediates. Hea ting of 5 with Et4NCN in DMSO provided 19, which was clearly derived f rom the proposed intermediate 17. Finally, imidazole 9 was converted i nto the ifluoromethyl)-1H-imidazol-5-yl]-N-methylbenzamide analogs, wh ich were potential acyl CoA:cholesterol acyltransferase (ACAT) inhibit ors.