Indole[1,2-c]quinazolines by Palladium-Catalyzed Cyclization of Bis(o-trifluoroacetamidophenyl) acetylene with Aryl and Vinyl Halides or Triflates

Antonio Arcadi; Sandro Cacchi; Alberto Cassetta; Giancarlo Fabrizi; Luca M. Parisi

doi:10.1055/s-2001-17458

Synlett 2001; 2001(10): 1605-1607
DOI: 10.1055/s-2001-17458

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Indole[1,2-c]quinazolines by Palladium-Catalyzed Cyclization of Bis(o-trifluoroacetamidophenyl) acetylene with Aryl and Vinyl Halides or Triflates

Antonio Arcadi^* , Sandro Cacchi, Alberto Cassetta, Giancarlo Fabrizi, Luca M. Parisi

^*Dipartimento di Chimica, Ing. Chimica e Materiali, Via Vetoio, 67100 L'Aquila, Italy; Fax + 39(6)49 91 27 80; E-mail: sandro.cacchi@uniromal.it

Abstract

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6-Trifluoromethyl-12-aryl(vinyl)indolo[1,2-c]quinazolines are prepared in high yield through the palladium-catalyzed reaction of readily available bis(o-trifluoroacetamidophenyl)acetylene with aryl or vinyl halides and triflates, followed by cyclization of the resultant derivatives. The reaction, which tolerates a variety of important functional groups, probably involves the 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.

indoloquinazolines - cyclization - palladium - catalysis - alkynes

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