2-Spirocyclopentane-1,2-dihydro-3H-indol-3-ones (namely, spiropseudo-indoxyls) constitute privileged scaffolds in organic synthesis and represent core components of different indole alkaloids (e.g. aristotelone and brevianamide A) and of molecules applied as functional dyes. In addition, they have found also an application as useful intermediate in the total synthesis of minfiensine. Taking into account these premises and our expertise in gold-catalyzed indole functionalization, we tested the reactivity of 4H-furo[3,2-b]indoles in the presence of electrophilic gold(I) activate π-systems (allenamides) with the aim to develop a new cascade process for the synthesis of these relevant scaffolds (Scheme 1). In this poster we present the obtained results together with the scope and limitation of the method and the proposed reaction mechanism.
Gold-catalyzed cascade reactions of 4H‐furo[3,2‐b]indoles with allenamides: synthesis of indolin-3-one derivatives / V. Pirovano, E. Brambilla, E. Rossi, G. Abbiati. ((Intervento presentato al 12. convegno International school of organometallic chemistry tenutosi a Camerino nel 2019.
Gold-catalyzed cascade reactions of 4H‐furo[3,2‐b]indoles with allenamides: synthesis of indolin-3-one derivatives
V. Pirovano
;E. Brambilla;E. Rossi;G. Abbiati
2019
Abstract
2-Spirocyclopentane-1,2-dihydro-3H-indol-3-ones (namely, spiropseudo-indoxyls) constitute privileged scaffolds in organic synthesis and represent core components of different indole alkaloids (e.g. aristotelone and brevianamide A) and of molecules applied as functional dyes. In addition, they have found also an application as useful intermediate in the total synthesis of minfiensine. Taking into account these premises and our expertise in gold-catalyzed indole functionalization, we tested the reactivity of 4H-furo[3,2-b]indoles in the presence of electrophilic gold(I) activate π-systems (allenamides) with the aim to develop a new cascade process for the synthesis of these relevant scaffolds (Scheme 1). In this poster we present the obtained results together with the scope and limitation of the method and the proposed reaction mechanism.File | Dimensione | Formato | |
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