Molecules 2013, 18(11), 13705-13722; doi:10.3390/molecules181113705
Article

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

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Received: 8 October 2013; in revised form: 1 November 2013 / Accepted: 4 November 2013 / Published: 6 November 2013
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.

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.

Chicago/Turabian Style

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.

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