A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

• Main Authors: Giovanni Palmisano, Andrea Penoni, Giancarlo Cravotto, Emanuela Calcio Gaudino, Luca Vaghi
• Format: Article
• Language: English
• Published: MDPI AG 2013-11-01
• Series: Molecules
• Subjects: oxcarbazepine; heteroannulation; library of compound; fused heterocycles; cyclization; cyclocondensation
• Online Access: http://www.mdpi.com/1420-3049/18/11/13705

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.