Merging the ability of cationic gold(I) catalysts to activate unsaturated π-systems with the electrophiles driven ring-opening reactions of furans, we describe a new approach to 2-spiroindolin-3-ones from 4H-furo[3,2-b]indoles. The reaction occurs through a cascade sequence involving addition of a gold-activated allene to the furan moiety of the starting furoindole followed by a ring-opening/ring-closing event affording 2-spirocyclopentane-1,2-dihydro-3H-indolin-3-ones in moderate to good yields.
Gold-Catalyzed Cascade Reactions of 4H-Furo[3,2-b]indoles with Allenamides: Synthesis of Indolin-3-one Derivatives / V. Pirovano, E. Brambilla, S. Rizzato, G. Abbiati, M. Bozzi, E. Rossi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - (2019 Mar). [Epub ahead of print] [10.1021/acs.joc.9b00143]
Gold-Catalyzed Cascade Reactions of 4H-Furo[3,2-b]indoles with Allenamides: Synthesis of Indolin-3-one Derivatives
V. Pirovano;E. Brambilla;S. Rizzato;G. Abbiati;E. Rossi
2019
Abstract
Merging the ability of cationic gold(I) catalysts to activate unsaturated π-systems with the electrophiles driven ring-opening reactions of furans, we describe a new approach to 2-spiroindolin-3-ones from 4H-furo[3,2-b]indoles. The reaction occurs through a cascade sequence involving addition of a gold-activated allene to the furan moiety of the starting furoindole followed by a ring-opening/ring-closing event affording 2-spirocyclopentane-1,2-dihydro-3H-indolin-3-ones in moderate to good yields.File | Dimensione | Formato | |
---|---|---|---|
E_Rossi_10.1021acs.joc.9b00143.pdf
Open Access dal 04/05/2020
Descrizione: Articolo principale
Tipologia:
Post-print, accepted manuscript ecc. (versione accettata dall'editore)
Dimensione
1.78 MB
Formato
Adobe PDF
|
1.78 MB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.