A straightforward one-pot approach to the synthesis of challenging 12-arylindolo[1,2-c]quinazolin-6(5H)-ones is described. Starting from readily available o-(o-aminophenylethynyl)trifluoroacetanilides, palladium-catalyzed aminoarylation of the triple bond with ArI, ArBr, and ArN2 +BF4 – 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.

Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quin­azolin-6(5 H )-ones / Arcadi, Antonio; Cacchi, Sandro; Fabrizi, Giancarlo; Ghirga, Francesca; Goggiamani, Antonella; Iazzetti, Antonia; Marinelli, Fabio. - In: SYNTHESIS. - ISSN 0039-7881. - 50:05(2018), pp. 1133-1140. [10.1055/s-0036-1589158]

Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quin­azolin-6(5 H )-ones

Cacchi, Sandro;Fabrizi, Giancarlo;Ghirga, Francesca;Goggiamani, Antonella;Iazzetti, Antonia
;
2018

Abstract

A straightforward one-pot approach to the synthesis of challenging 12-arylindolo[1,2-c]quinazolin-6(5H)-ones is described. Starting from readily available o-(o-aminophenylethynyl)trifluoroacetanilides, palladium-catalyzed aminoarylation of the triple bond with ArI, ArBr, and ArN2 +BF4 – 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.
elimination; indoles; palladium; polycycles; quinazolinones; trifluoromethane; catalysis; organic chemistry
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Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quin­azolin-6(5 H )-ones / Arcadi, Antonio; Cacchi, Sandro; Fabrizi, Giancarlo; Ghirga, Francesca; Goggiamani, Antonella; Iazzetti, Antonia; Marinelli, Fabio. - In: SYNTHESIS. - ISSN 0039-7881. - 50:05(2018), pp. 1133-1140. [10.1055/s-0036-1589158]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1071338
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