3-OXO-4,4,4-TRIFLUOROBUTYRONITRILES AS BUILDING-BLOCKS OF TRIFLUOROMETHYL-SUBSTITUTED HETEROCYCLES .2. HETEROCYCLIZATION TO 3-ARYL-4-TRIFLUOROMETHYL-2H-1-BENZOPYRAN-2-ONES UNDER HOESCH REACTION CONDITIONS
T. Nishiwaki et H. Kikukawa, 3-OXO-4,4,4-TRIFLUOROBUTYRONITRILES AS BUILDING-BLOCKS OF TRIFLUOROMETHYL-SUBSTITUTED HETEROCYCLES .2. HETEROCYCLIZATION TO 3-ARYL-4-TRIFLUOROMETHYL-2H-1-BENZOPYRAN-2-ONES UNDER HOESCH REACTION CONDITIONS, Journal of heterocyclic chemistry, 31(4), 1994, pp. 889-891
Resorcinol and 5-methylresorcinol, respectively, react with 3-oxo-2-ar
yl-4,4,4-trifluorobutyronitrile using zinc chloride as a catalyst in d
ibutyl ether under the Hoesch reaction conditions to give a low yield
of 3-aryl-7-hydoxy-4-trifluoromethyl- or 7-methyl-4-trifluoromethyl-2H
-1-benzopyran-2-ones. However, the related reaction with m-methoxyphen
ol was found to produce poor yields of -7-methoxy-4-trifluoromethyl-2H
-1-benzopyran-2-one and its 3,4-dihydro-4-hydroxy derivative.