RESUMO
Various readily available, Ugi-derived dehydroalanines were used as pivotal templates to easily and efficiently assemble diverse pharmacologically important polyheterocyclic systems through cascade palladium-catalyzed C-C bond formation processes. Allyl, homoallyl and propargylamine led to the formation of benzopyrrolizidinones, benzoindolizidinones and pyrazinoisoquinolines, respectively, while benzylamines and o-bromobenzylamines were used as precursors of tetracyclic-fused systems and pyrazionoisoquinolindiones.
Assuntos
Alanina/análogos & derivados , Alanina/química , Benzilaminas/química , Catálise , Indóis/química , Isoquinolinas/química , Paládio/química , Pirróis/químicaRESUMO
A series of nine novel 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones were prepared in moderate to good overall yields in only two reaction steps. The first step consisted of a one-pot sequential process of an Ugi-azide multicomponent reaction, N-acylation and SN2 to give the xanthates. The second step was an intramolecular cyclization under free radical conditions. Also, their binding modes have been modelled using docking techniques.