N. Sewald et K. Burger, REACTIONS OF 3,3,3-TRIFLUOROPYRUVATES WITH AMIDINES - NEW TRIFLUOROMETHYL-SUBSTITUTED HETEROCYCLIC BUILDING-BLOCKS, Monatshefte fuer Chemie, 124(8-9), 1993, pp. 899-907
4-Hydroxy-4-trifluoromethyl-2-imidazolin-5-ones are obtained in good y
ields upon reaction of 3,3,3-trifluoropyruvates with amidines. Subsequ
ent treatment of these heterocycles with thionyl chloride gives 4-chlo
ro-4-trifluoromethyl-2-imidazolin-5-ones which proved to be versatile
trifluoromethyl substituted building blocks. Substitution of chloride
is feasible with a variety of hetero and carbon nucleophiles. Ring exp
ansion with diazo compounds affords trifluoromethyl substituted pyrimi
dines.