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Synlett 2001; 2001(10): 1605-1607
DOI: 10.1055/s-2001-17458
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
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Publication History
Publication Date:
27 September 2001 (online)
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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