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 a-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 a-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. © 2013 by the authors.