A straightforward one-pot approach to the synthesis of challenging 12-arylindolo[1,2- c ]quinazolin-6(5 H)-ones is described. Starting from readily available o -(o -aminophenylethynyl)trifluoroacetanilides, palladium-catalyzed aminoarylation of the triple bond with ArI, ArBr, and ArN 2+ BF 4- is followed by cyclization of the resulting N -trifluoroacetyl-2-(o -aminophenyl)-3-aryl indole. This sequential reaction provides the title compounds by means of a rare elimination of trifluoromethane.
Arcadi, A., Cacchi, S., Fabrizi, G., Ghirga, F., Goggiamani, A., Iazzetti, A., Marinelli, F., Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quinazolin-6(5 H)-ones, <<SYNTHESIS>>, 2018; 50 (5): 1133-1140. [doi:10.1055/s-0036-1589158] [http://hdl.handle.net/10807/200463]
Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quinazolin-6(5 H)-ones
Iazzetti, Antonia
;
2018
Abstract
A straightforward one-pot approach to the synthesis of challenging 12-arylindolo[1,2- c ]quinazolin-6(5 H)-ones is described. Starting from readily available o -(o -aminophenylethynyl)trifluoroacetanilides, palladium-catalyzed aminoarylation of the triple bond with ArI, ArBr, and ArN 2+ BF 4- is followed by cyclization of the resulting N -trifluoroacetyl-2-(o -aminophenyl)-3-aryl indole. This sequential reaction provides the title compounds by means of a rare elimination of trifluoromethane.
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