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

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

1
,
2
,
1
 and
1,*
1 Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago 7820436, Chile 2 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)
Download PDF [257 KB, 18 June 2014; original version 18 June 2014]

Abstract

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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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