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Molecules 2013, 18(12), 14797-14806; doi:10.3390/molecules181214797

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

Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago 7820436, Chile
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid 28040, Spain
Author to whom correspondence should be addressed.
Received: 14 November 2013 / Revised: 26 November 2013 / Accepted: 26 November 2013 / Published: 29 November 2013
(This article belongs to the Section Organic Synthesis)
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In this report a short and efficient synthesis of the dibenz[b,f]oxepin framework through intramolecular SNAr 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 TiCl4/Zn in THF gave the target dibenzo[b,f]oxepin system in 53%–55% yields.
Keywords: dibenzoxepins; Wittig reaction; McMurry reaction; aromatic nucleophilic substitution dibenzoxepins; Wittig reaction; McMurry reaction; aromatic nucleophilic substitution

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

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MDPI and ACS Style

Moreno, D.R.R.; Giorgi, G.; Salas, C.O.; Tapia, R.A. New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold. Molecules 2013, 18, 14797-14806.

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