Next Article in Journal
Headspace Solid-Phase Microextraction Analysis of Volatile Components in Narcissus tazetta var. chinensis Roem
Previous Article in Journal
Deep Oxidative Desulfurization of Dibenzothiophene in Simulated Oil and Real Diesel Using Heteropolyanion-Substituted Hydrotalcite-Like Compounds as Catalysts
Article Menu

Export Article

Open AccessArticle
Molecules 2013, 18(11), 13705-13722; https://doi.org/10.3390/molecules181113705

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

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.
Received: 8 October 2013 / Revised: 1 November 2013 / Accepted: 4 November 2013 / Published: 6 November 2013
(This article belongs to the Section Organic Chemistry)
View Full-Text   |   Download PDF [378 KB, uploaded 18 June 2014]   |  

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. View Full-Text
Keywords: oxcarbazepine; heteroannulation; library of compound; fused heterocycles; cyclization; cyclocondensation oxcarbazepine; heteroannulation; library of compound; fused heterocycles; cyclization; cyclocondensation
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top