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

Antonio Arcadi; Sandro Cacchi; Giancarlo Fabrizi; Francesca Ghirga; Antonella Goggiamani; Antonia Iazzetti; Fabio Marinelli

doi:10.1055/s-0036-1589158

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

Antonio Arcadi, Sandro Cacchi, Giancarlo Fabrizi, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti^*, Fabio Marinelli^*

^*Autore corrispondente per questo lavoro

Risultato della ricerca: Contributo in rivista › Articolo in rivista

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.

Lingua originale	English
pagine (da-a)	1133-1140
Numero di pagine	8
Rivista	Synthesis
Volume	50
DOI	https://doi.org/10.1055/s-0036-1589158
Stato di pubblicazione	Pubblicato - 2018

Keywords

elimination
indoles
palladium
polycycles
quinazolinones
trifluoromethane

Accesso al documento

10.1055/s-0036-1589158

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

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.",

keywords = "elimination, indoles, palladium, polycycles, quinazolinones, trifluoromethane, elimination, indoles, palladium, polycycles, quinazolinones, trifluoromethane",

author = "Antonio Arcadi and Sandro Cacchi and Giancarlo Fabrizi and Francesca Ghirga and Antonella Goggiamani and Antonia Iazzetti and Fabio Marinelli",

year = "2018",

doi = "10.1055/s-0036-1589158",

language = "English",

volume = "50",

pages = "1133--1140",

journal = "Synthesis",

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TY - JOUR

T1 - Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quinazolin-6(5 H)-ones

AU - Arcadi, Antonio

AU - Cacchi, Sandro

AU - Fabrizi, Giancarlo

AU - Ghirga, Francesca

AU - Goggiamani, Antonella

AU - Iazzetti, Antonia

AU - Marinelli, Fabio

PY - 2018

Y1 - 2018

N2 - 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.

AB - 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.

KW - elimination

KW - indoles

KW - palladium

KW - polycycles

KW - quinazolinones

KW - trifluoromethane

KW - elimination

KW - indoles

KW - palladium

KW - polycycles

KW - quinazolinones

KW - trifluoromethane

UR - http://hdl.handle.net/10807/200463

U2 - 10.1055/s-0036-1589158

DO - 10.1055/s-0036-1589158

M3 - Article

SN - 0039-7881

VL - 50

SP - 1133

EP - 1140

JO - Synthesis

JF - Synthesis

ER -

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

Abstract

Keywords

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