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.

Vaghi, L., Gaudino, E., Cravotto, G., Palmisano, G., & Penoni, A. (2013). A structurally diverse heterocyclic library by decoration of oxcarbazepine scaffold. MOLECULES, 18(11), 13705-13722 [10.3390/molecules181113705].

A structurally diverse heterocyclic library by decoration of oxcarbazepine scaffold

Vaghi, Luca
Primo
;
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 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.
Articolo in rivista - Articolo scientifico
Cyclization; Cyclocondensation; Fused heterocycles; Heteroannulation; Library of compound; Oxcarbazepine; Carbamazepine; Heterocyclic Compounds; Magnetic Resonance Spectroscopy; Molecular Structure; Medicine (all); Organic Chemistry
English
13705
13722
18
Vaghi, L., Gaudino, E., Cravotto, G., Palmisano, G., & Penoni, A. (2013). A structurally diverse heterocyclic library by decoration of oxcarbazepine scaffold. MOLECULES, 18(11), 13705-13722 [10.3390/molecules181113705].
Vaghi, L; Gaudino, E; Cravotto, G; Palmisano, G; Penoni, A
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/194293
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