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 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; in revised form: 26 November 2013 / Accepted: 26 November 2013 / Published: 29 November 2013
(This article belongs to the Section Organic Synthesis)
PDF Full-text Download PDF Full-Text [257 KB, Updated Version, uploaded 5 December 2013 16:14 CET]
The original version is still available [272 KB, uploaded 29 November 2013 11:04 CET]
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

Supplementary Files

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

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.

AMA Style

Moreno DRR, Giorgi G, Salas CO, Tapia RA. New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold. Molecules. 2013; 18(12):14797-14806.

Chicago/Turabian Style

Moreno, David R.R.; Giorgi, Giorgio; Salas, Cristian O.; Tapia, Ricardo A. 2013. "New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold." Molecules 18, no. 12: 14797-14806.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert