New short strategy for the synthesis of the dibenz[b,f]oxepin scaffold

David R R Moreno; Giorgio Giorgi; Cristian O Salas; Ricardo A Tapia

doi:10.3390/molecules181214797

New short strategy for the synthesis of the dibenz[b,f]oxepin scaffold

Molecules. 2013 Nov 29;18(12):14797-806. doi: 10.3390/molecules181214797.

Authors

David R R Moreno, Giorgio Giorgi, Cristian O Salas, Ricardo A Tapia¹

Affiliation

¹ Departamento de Química Orgánica, Facultad de Química, Pontificia Universidad Católica de Chile, Santiago 7820436, Chile. rtapia@uc.cl.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Combinatorial Chemistry Techniques
Microwaves
Molecular Structure
Oxepins / chemical synthesis*
Oxepins / chemistry

Substances

Oxepins