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A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell' Insubria, via Valleggio 11, Como 22038, Italy
Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, via Giuria 9, Torino 10125, Italy
* Author to whom correspondence should be addressed.
Received: 8 October 2013; in revised form: 1 November 2013 / Accepted: 4 November 2013 / Published: 6 November 2013
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.
Keywords: oxcarbazepine; heteroannulation; library of compound; fused heterocycles; cyclization; cyclocondensation
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MDPI and ACS Style
Vaghi, L.; Gaudino, E.C.; Cravotto, G.; Palmisano, G.; Penoni, A. A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold. Molecules 2013, 18, 13705-13722.
Vaghi L, Gaudino EC, Cravotto G, Palmisano G, Penoni A. A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold. Molecules. 2013; 18(11):13705-13722.
Vaghi, Luca; Gaudino, Emanuela C.; Cravotto, Giancarlo; Palmisano, Giovanni; Penoni, Andrea. 2013. "A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold." Molecules 18, no. 11: 13705-13722.