12-Acylindolo[1,2-c]quinazolines by palladium-catalyzed cyclocarbonylation of o-alkynyltrifluoroacetanilides.
6-Trifluoromethyl-12-acylindolo[1,2-c]quinazolines are prepared in high yield through the palladium-catalyzed reaction of bis(o-trifluoroacetamidophenyl)acetylene with aryl or vinyl halides and triflates. The reaction, which tolerates a variety of important functional groups, probably involves the formation of a 3-acyl-2-(o-trifluoroacetamidophenyl)indole intermediate, followed by its cyclization to the indoloquinazoline product. [reaction: see text]
Battistuzzi
Gianfranco
G
Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università degli Studi La Sapienza, P.le A. Moro 5, 00185 Rome, Italy.
Cacchi
Sandro
S
Fabrizi
Giancarlo
G
Marinelli
Fabio
F
Parisi
Luca M
LM
D000083:Acetanilides / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D002013:Bryozoa / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D010165:Palladium / Q000737:chemistry*
D000083:Acetanilides; D000480:Alkynes; D010165:Palladium