A. Arcadi et al., Indole[1,2-c]quinazolines by palladium-catalyzed cyclization of bis(o-trifluoroacetamidophenyl) acetylene with aryl and vinyl halides or triflates, SYNLETT, (10), 2001, pp. 1605-1607
6-Trifluoromethyl-12-aryl(vinyl)indolo[1,2-c]quinazolines are prepared in h
igh yield through the palladium-catalyzed reaction of readily available bis
(o-trifluoroacetamidophenyl)acetylene with aryl or vinyl halides and trifla
tes. followed by cyclization of the resultant derivatives. The reaction, wh
ich tolerates a variety of important functional groups. probably involves t
he formation of a 3-aryl-2-(o-trifluoroacetamidophenyl)indole intermediate,
followed by its cyclization to the indolequinazoline product. Formation of
the indoloquinazoline nucleus has been unambiguously determined via X-ray
analysis.