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Article

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

by
Luca Vaghi
1,*,
Emanuela Calcio Gaudino
2,
Giancarlo Cravotto
2,
Giovanni Palmisano
1 and
Andrea Penoni
1
1
Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell' Insubria, via Valleggio 11, Como 22038, Italy
2
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.
Molecules 2013, 18(11), 13705-13722; https://doi.org/10.3390/molecules181113705
Submission received: 8 October 2013 / Revised: 1 November 2013 / Accepted: 4 November 2013 / Published: 6 November 2013
(This article belongs to the Section Organic Chemistry)
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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 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. https://doi.org/10.3390/molecules181113705

AMA Style

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. https://doi.org/10.3390/molecules181113705

Chicago/Turabian Style

Vaghi, Luca, Emanuela Calcio Gaudino, Giancarlo Cravotto, Giovanni Palmisano, and Andrea Penoni. 2013. "A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold" Molecules 18, no. 11: 13705-13722. https://doi.org/10.3390/molecules181113705

APA Style

Vaghi, L., Gaudino, E. C., Cravotto, G., Palmisano, G., & Penoni, A. (2013). A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold. Molecules, 18(11), 13705-13722. https://doi.org/10.3390/molecules181113705

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