title: A structurally diverse heterocyclic library by decoration of oxcarbazepine scaffold.
abstract: 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.
authors.affiliation: Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell' Insubria, via Valleggio 11, Como 22038, Italy. luca.vaghi@uninsubria.it.
authors.forename: Luca
authors.initials: L
authors.lastname: Vaghi
authors.forename: Emanuela Calcio
authors.initials: EC
authors.lastname: Gaudino
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Cravotto
authors.forename: Giovanni
authors.initials: G
authors.lastname: Palmisano
authors.forename: Andrea
authors.initials: A
authors.lastname: Penoni
mesh_terms: D002220:Carbamazepine / Q000031:analogs & derivatives* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D000078330:Oxcarbazepine
chemical_list: D006571:Heterocyclic Compounds; D002220:Carbamazepine; D000078330:Oxcarbazepine