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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of Selenylated Dibenzo[b,f]oxepines from an Electrophilic Cyclization Reaction
Liliane S de Farias1, Sabrina B Acosta2, Luiz H Dapper1
1Núcleo de Estudo Estrutural e Síntese de HeterociclosNEESH, Universidade Federal do Rio GrandeFURG, Escola de Química e AlimentosEQA, Itália Ave., km 8, no numberCampus Carreiros, Rio Grande, RS 96203-900, Brazil.
Abstract:
An efficient FeCl3-mediated intramolecular cyclization of o-alkynyl diaryl ethers with diorganyl diselenides has been developed, providing selenylated dibenzo-[b,f]-oxepines in good to excellent yields under mild conditions. The optimized protocol using 0.6 equiv of diorganyl diselenide and 1 equiv of FeCl3 in DCM at room temperature exhibited a broad substrate scope and high tolerance toward diverse functional groups. This approach occurs by in situ formation of an electrophilic selenium species, which undergoes a 7-endo-dig cyclization to furnish the heterocyclic core. This method provides straightforward access to functionalized dibenzo-[b,f]-oxepines containing selenium, a motif of interest due to its relevance in medicinal chemistry and materials science.
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