New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold

In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular S(N)Ar and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylalde...

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Autores principales: Moreno, David R. R., Giorgi, Giorgio, Salas, Cristian O., Tapia, Ricardo A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270238/
https://www.ncbi.nlm.nih.gov/pubmed/24352054
http://dx.doi.org/10.3390/molecules181214797
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author Moreno, David R. R.
Giorgi, Giorgio
Salas, Cristian O.
Tapia, Ricardo A.
author_facet Moreno, David R. R.
Giorgi, Giorgio
Salas, Cristian O.
Tapia, Ricardo A.
author_sort Moreno, David R. R.
collection PubMed
description In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular S(N)Ar and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylaldehydes with fluorobenzaldehydes without catalysts. Application of an intramolecular McMurry reaction to the synthesized diarylethers using TiCl(4)/Zn in THF gave the target dibenzo[b,f]oxepin system in 53%–55% yields.
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spelling pubmed-62702382018-12-20 New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold Moreno, David R. R. Giorgi, Giorgio Salas, Cristian O. Tapia, Ricardo A. Molecules Article In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular S(N)Ar and McMurry reactions is described. The diaryl ethers required for the McMurry reaction have been obtained in good yields under microwave-assisted conditions of the reaction of salicylaldehydes with fluorobenzaldehydes without catalysts. Application of an intramolecular McMurry reaction to the synthesized diarylethers using TiCl(4)/Zn in THF gave the target dibenzo[b,f]oxepin system in 53%–55% yields. MDPI 2013-11-29 /pmc/articles/PMC6270238/ /pubmed/24352054 http://dx.doi.org/10.3390/molecules181214797 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Moreno, David R. R.
Giorgi, Giorgio
Salas, Cristian O.
Tapia, Ricardo A.
New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_full New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_fullStr New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_full_unstemmed New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_short New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold
title_sort new short strategy for the synthesis of the dibenz[b,f]oxepin scaffold
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270238/
https://www.ncbi.nlm.nih.gov/pubmed/24352054
http://dx.doi.org/10.3390/molecules181214797
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