Cargando…

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

A library of new heterocyclic systems was synthesized starting from oxcarbazepine (OXC, Trileptal(®), 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide). The key for these transformations is the α-enolizable ketone present on the [d]-side of our starting material OXC, thus, an in depth inves...

Descripción completa

Detalles Bibliográficos
Autores principales: Vaghi, Luca, Gaudino, Emanuela Calcio, Cravotto, Giancarlo, Palmisano, Giovanni, Penoni, Andrea
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270634/
https://www.ncbi.nlm.nih.gov/pubmed/24201207
http://dx.doi.org/10.3390/molecules181113705
Descripción
Sumario:A library of new heterocyclic systems was synthesized starting from oxcarbazepine (OXC, Trileptal(®), 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide). The key for these transformations is the α-enolizable ketone present on the [d]-side of our starting material OXC, thus, an in depth investigation of the literature to find heteroannulation reactions for substrates carrying an α-enolizable ketone gave us a boost to discover an excellent derivatization strategy and [3+2], [4+2] and [4+1] approaches were successfully developed. Almost always a pre-functionalization was needed, but also the direct one-pot heterocycle construction was also explored.